6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

ABSTRACT

Disclosed are triazine derivative compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides.

TECHNICAL FIELD

The present invention relates to a novel triazine derivative or its salt, and herbicides containing it as an effective component.

BACKGROUND ART

Triazine derivatives are known from “Collection of Czechoslovak Chemical Communications (1969), 34(6), 1673-83,” etc., for example. However, no herbicidal activity is described for the compounds disclosed in these literatures. Although various compounds are reported as triazine-based herbicides (for example, see “The Pesticide Manual 15th Edition, 2009, published by BCPC”), they all have a 1,3,5-triazine ring. Specific examples of the 1,3,5-triazine-based agrochemicals include 2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (Simazine), 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (Atrazin), 2,4-bis(ethylamino)-6-methylthio-1,3,5-triazine (Simetryn), 2,4-bis(isopropylamino)-6-methylthio-1,3,5-triazine (Prometryn), and 2-(1,2-dimethylpropylamino)-4-ethylamino-6-methylthio-1,3,5-triazine (Dimethametryn).

Further, as a 1,2,4-triazine-based agrochemical, there are known 4-amino-3-methyl-6-phenyl-1,2,4-triazine-5(4H)-one (Metamitron), 4-amino-6-tert-butyl-3-methylthio-1,2,4-triazine-5(4H)-one (Metribuzin), etc. It is disclosed in Japanese Patent Application Laid-Open (JP-A) No. 8-259546 that 4-(2,4-dihalogeno-5-alkoxyphenyl)-1,2,4-triazine-3,5-dione derivatives having a hydrocarbon substituent group at 6-position have a herbicidal activity. It is disclosed in JP-A No. 5-51369 that 3,5-diaryl-6-amino-1,2,4-triazine derivatives have a herbicidal activity. It is disclosed in JP-A No. 5-32641 that 3-mercapto-1,2,4-triazine derivatives have a herbicidal activity.

However, it is not known from any literatures that 6-acyl-1,2,4-triazine-3,5-dione derivatives represented by Formula 1 below have a herbicidal activity.

CITATION LIST Patent Literature

-   PLT 1: Japanese Patent Application Laid-Open No. 8-259546 -   PLT 2: Japanese Patent Application Laid-Open No. 5-51369 -   PLT 3: Japanese Patent Application Laid-Open No. 5-32641

Non Patent Literature

-   NPL 1: Collection of Czechoslovak Chemical Communications (1969),     34(6), 1673-83. -   NPL 2: The Pesticide Manual 15th Edition (2009, published by BCPC)

SUMMARY OF INVENTION Technical Problem

Herbicides used for useful crops and useful plants are required to be a chemical preparation which can be applied to soils or leaves and exhibit a sufficient herbicidal effect with low chemical dosage. Further, as there is an increasing need concerning safety and effect on environment of a chemical substance, development of safer herbicides is waited for. The invention is devised to cope with such problems.

Solution to Problem

In order to achieve the object above, inventors of the invention synthesized many triazine compounds to study the herbicidal activity of various triazine derivatives, and intensively determined the herbicidal activity and usefulness of the compounds. As a result, it is found that, when triazine derivatives of the invention are applied to weeds or soils wherein weeds thrive, an excellent herbicidal effect is obtained for a long period of time, and therefore the invention is completed accordingly.

Thus, the present invention relates to the following (1) to (43).

(1) A triazine derivative or a salt thereof represented by following Formula 1:

[in the formula, R¹ represents a hydrogen atom; a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; an amino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylamino C₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a hydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group (phenyl in the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α); a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α): a phenylthio C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenylsulfinyl C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenylsulfonyl C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a C₁-C₆ haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a phenoxyimino C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a di(C₁-C₆ alkoxy)C₁-C₆ alkyl group; a (R³¹R³²N—C═O)C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone]; a C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α]; a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α]; or a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α];

R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the Substituent group α; or a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the Substituent group α,

Y and Z represent an oxygen atom or a sulfur atom,

“A” represents any one of the following formula A-1 to A-5,

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metal cation or an ammonium cation); an amino group; a halogen atom; a cyano group; an isothiocyanate group; an isocyanate group; a hydroxycarbonyloxy group; a C₂-C₆ alkoxycarbonyloxy group; a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group α; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a cyanomethylene oxy group; a C₃-C₆ cycloalkyl C₂-C₆ alkyloxy group; a C₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkylcarbonyloxy group; a C₂-C₆ alkenylcarbonyloxy group; a C₂-C₆ haloalkenylcarbonyloxy group; a C₂-C₆ alkynylcarbonyloxy group; a C₂-C₆ haloalkynylcarbonyloxy group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group; a phenyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a benzyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a phenylcarbonyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a benzylcarbonyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a phenylcarbonyl C₁-C₆ alkyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₁₀ alkylsulfonlyoxy group; a C₁-C₆ haloalkylsulfonlyoxy group; a phenylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a benzylsulfonyloxy group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₁₀ alkylthio group; a C₁-C₁₀ alkylsulfinyl group; a C₁-C₁₀ alkylsulfonyl group; a C₁-C₆ haloalkylthio group; a C₁-C₆ haloalkylsulfinyl group; a C₁-C₆ haloalkylsulfonyl group; a C₂-C₆ alkenylthio group; a C₂-C₆ alkenylsulfinyl group; a C₂-C₆ alkenylsulfonyl group; a C₂-C₆ alkynylthio group; a C₂-C₆ alkynylsulfinyl group; a C₂-C₆ alkynylsulfonyl group; a phenylthio group which may be substituted with one or more substituents selected from the Substituent group α; a benzylthio group which may be substituted with one or more substituents selected from the Substituent group α; a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group α; a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₁₀ alkylamino group; a di(C₁-C₁₀ alkyl)amino group; a C₁-C₆ alkoxycarbonylamino group; a C₁-C₆ alkoxy group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); or a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α),

A₁ represents a group represented by the following formula

A₂ represents a group represented by the following formula

A₃ represents a group represented by the following formula

n represents 0, 1, or 2,

R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group, herein, R⁵ and R⁸ may be joined together to form a C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain to form a ring with adjacent carbon atoms,

R⁷, R³³, and R³⁴ each independently represent a hydrogen atom, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, or a C₁-C₆ alkoxy group,

R¹⁴, R¹⁵, R¹⁶, and R¹⁷ each independently represent a hydrogen atom, a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, or a benzyl group which may be substituted with one or more substituents selected from the Substituent group α,

R¹⁸ represents a hydrogen atom, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a cyanomethyl group, or a benzyl group,

R²⁰ represents a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, or a C₃-C₆ cycloalkyl C₁-C₆ alkyl group,

R²¹ represents a hydrogen atom, a C₁-C₆ alkyl group, or a halogen atom,

R²³ represents a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₃-C₆ cycloalkyl group, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinyl group, a C₁-C₁₀ alkylsulfonyl group, a phenylthio group which may be substituted with one or more substituents selected from the Substituent group α, a benzylthio group which may be substituted with one or more substituents selected from the Substituent group α, a phenylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group α, a benzylsulfinyl group which may be substituted with one or more substituents selected from the Substituent group α, a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α, or a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α,

R²⁴ represents a hydrogen atom, a halogen atom, a cyano group, a C₁-C₆ alkyl group, a C₃-C₆ cycloalkyl group, or a C₁-C₆ alkoxycarbonylamino group,

R²⁵ represents a C₁-C₆ alkoxycarbonyl group, a cyano group, or a nitro group,

R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a benzyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl group; a C₁-C₁₀ alkylthio carbonyl group; a C₁-C₆ alkoxycarbonyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the Substituent group α; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); or a C₁-C₆ alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α), herein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom.

Herein, “Substituent group α” represents a group selected from a group consisting of:

a halogen atom; a hydroxyl group; a C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a C₁-C₆ haloalkylthio group; a C₁-C₆ haloalkylsulfinyl group; a C₁-C₆ haloalkylsulfonyl group; an amino group; a C₁-C₆ alkylcarbonylamino group; a mono(C₁-C₆ alkyl)amino group; a di(C₁-C₆ alkyl)amino group; a hydroxy C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy C₁-C₆ alkoxy group; a cyano C₁-C₆ alkoxy group; a C₁-C₆ acyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a carboxyl group; a C₁-C₆ alkoxycarbonyl group; a carbamoyl group; a mono(C₁-C₆ alkyl)aminocarbonyl group; a di(C₁-C₆ alkyl)aminocarbonyl group; a nitro group; a cyano group; a phenyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); and a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and

“Substituent group β” represents a group selected from a group consisting of: a halogen atom, a nitro group, a cyano group, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₁-C₆ alkoxy group, and a C₁-C₆ haloalkoxy group.].

(2) The triazine derivative or the salt thereof according to (1), wherein A in Formula 1 is A-1. (3) The triazine derivative or the salt thereof according to (1) or (2), wherein in A-1, A₁ is [X₁], A₂ is [X₃], and A₃ is [X₉]. (4) The triazine derivative or the salt thereof according to (3), wherein R⁵ and R⁶ in [X₁] is a hydrogen atom or a C₁-C₆ alkyl group, R⁸ and R⁹ in [X₃] is a hydrogen atom or a C₁-C₆ alkyl group, and R³⁵ and R³⁶ in [X₉] is a hydrogen atom or a C₁-C₆ alkyl group, or R⁵ and R³⁵ may bind to each other via a C₁-C₅ alkylene chain to form a ring. (5) The triazine derivative or the salt thereof according to (1), wherein A in Formula 1 is A-3. (6) The triazine derivative or the salt thereof according to (5), wherein R²⁰ in A-3 is a C₁-C₆ alkyl group, and R21 in A-3 is a hydrogen atom or a C₁-C₆ alkyl group. (7) The triazine derivative or the salt thereof according to any one of (1) to (6), wherein R⁴ in A-1 is a hydroxyl group or an O⁻M⁺ (M⁺ represents an alkali metal cation or an ammonium cation). (8) The triazine derivative or the salt thereof according to any one of (1) to (7), wherein Y in Formula 1 is an oxygen atom. (9) The triazine derivative or the salt thereof according to any one of (1) to (8), wherein R in Formula 1 is the group selected from the group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone]. (10) The triazine derivative or the salt thereof according to any one of (1) to (9), wherein R² in Formula 1 is the group selected from the group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α). (11) The triazine derivative or the salt thereof according to (1), in which the groups in Formula 1 are as follows: R¹ represents a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenylthio C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenylsulfinyl C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenylsulfonyl C₁-C₆ alkyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a NR³¹R³² group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); or a C₁-C₆ alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α);

R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; or a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1, A-3, and A-5,

A₁ is [X₁],

A₂ is [X₃] or [X₄], and

A₃ is [X₉],

in [X₁], R⁵ and R⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

in [X₃], R⁸ and R⁹ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

in [X₉], R³⁵ and R³⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

herein, R⁵ and R⁸ may be joined together to form a C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain to form a ring with adjacent carbon atoms,

in A-3, R²⁰ is a C₁-C₆ alkyl group,

R²¹ is a hydrogen atom or a C₁-C₆ alkyl group,

in A-5, R²⁴ represents a hydrogen atom, a C₁-C₆ alkyl group, or a C₃-C₆ cycloalkyl group, R²⁵ represents a C₁-C₆ alkoxycarbonyl group, a cyano group, or a nitro group,

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metal cation or an ammonium cation); or a C₁-C₁₀ alkylsulfonlyoxy group;

R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; or a benzyl group which may be substituted with one or more substituents selected from the Substituent group α; herein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom,

herein, “Substituent group α” represents a group selected from a group consisting of:

a halogen atom; a C₃-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group (the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 heteroatoms that are optionally selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group β); and a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group.

(12) The triazine derivative or the salt thereof according to (1), in which the groups in Formula 1 are as follows:

R¹ is a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a NR³¹R³² group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and, a C₁-C₆ alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α);

R³¹ and R³² each independently represent a group selected from a group consisting of a hydrogen atom; a C₁-C₆ alkyl group; and, a phenyl group which may be substituted with one or more substituents selected from the Substituent group α;

R² represents a group selected from a group consisting of a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α); and, a phenyl group which may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1, A-3, and A-5,

R⁴ in A-1 represents a hydroxyl group;

O⁻M⁺ (M⁺ represents an alkali metal cation or an ammonium cation);

or a C₁-C₁₀ alkylsulfonyloxy group;

in A-1, A₁ is [X₁],

A₂ is [X₃] or [X₄], and

A₃ is [X₉],

in [X₁], R⁵ and R⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

in [X₃], R⁸ and R⁹ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

in [X₉], R³⁵ and R³⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group,

herein, R⁵ and R⁸ may bind to each other via a C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain to form a ring, and R⁵ and R³⁵ may bind to each other via a C₁-C₅ alkylene chain to form a ring,

in A-3, R²⁰ is a C₁-C₆ alkyl group,

R²¹ is a hydrogen atom or a C₁-C₆ alkyl group, and

R⁴ represents a hydroxyl group; O⁻M⁺ (M⁺ represents an alkali metal cation or an ammonium cation); or a C₁-C₁₀ alkylsulfonlyoxy group;

“Substituent group α” represents a group selected from a group consisting of: a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group.

(13) The triazine derivative or the salt thereof according to (1), in which the groups in Formula 1 are as follows:

R¹ represents a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a NR³¹R³² group; a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyridazinyl group, thienyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, pyrazinyl group, piperidinyl group, and piperazinyl group (the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and, a tetrahydrofuryl-methyl group;

R³¹ and R³² each independently represent a group selected from a group consisting of a hydrogen atom; a C₁-C₆ alkyl group; and a phenyl group;

R² represents a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a pyridyl group; and a phenyl group;

Y and Z represent an oxygen atom or a sulfur atom,

A represents any one of A-1 and A-3,

R⁴ in A-1 represents a hydroxyl group; or a C₁-C₁₀ alkylsulfonlyoxy group,

in A-1, A₁ is [X₁], A₂ is [X₃] or [X₄], and A₃ is [X₉],

in [X₁], R⁵ and R⁶ are a hydrogen atom or a C₁-C₆ alkyl group,

in [X₃], R⁸ and R⁹ are a hydrogen atom or a C₁-C₆ alkyl group,

in [X₂], R³⁵ and R³⁶ are a hydrogen atom or a C₁-C₆ alkyl group,

herein, R⁵ and R⁸ may be joined together to form a C₂-C₅ alkylene chain and to form a ring,

and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain and to form a ring,

in A-3, R²⁰ is a C₁-C₆ alkyl group, R²¹ is a hydrogen atom or a C₁-C₆ alkyl group, and R⁴ represents a hydroxyl group or a C₁-C₁₀ alkylsulfonlyoxy group, and

“Substituent group α” represents a group selected from a group consisting of: a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; a C₁-C₆ haloalkoxy group; a C₂-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.

(14) An agrochemical composition comprising the triazine derivative or the salt thereof described in any one of (1) to (13), and an agriculturally acceptable carrier. (15) The agrochemical composition according to (14), in which the agrochemical composition further comprises a surface active agent. (16) A herbicide comprising the triazine derivative or the salt thereof described in any one of (1) to (13) as an active component. (17) The herbicide according to (16), in which the herbicide has a herbicidal activity for weeds in a field or a paddy field in which agrohorticultural plants are cultivated. (18) The herbicide according to (17), in which the agrohorticultural plants are agrohorticultural plants given with resistance by a breeding method or a genetic recombination technique. (19) A method of eliminating weeds in soils by applying an effective amount of herbicides comprising the triazine derivative or the salt thereof described in any one of (16) to (18). (20) The method according to (19), in which the soils are a farmland. (21) The method according to (19), in which the farmland is a field or a paddy field in which agrohorticultural plants are cultivated. (22) A triazine derivative or a salt thereof represented by following Formula 2:

[in the formula, B represents a hydroxyl group or a C₁-C₆ alkoxy group and R¹, R², Y and Z have the same definitions as those described in above Formula 1].

(23) The triazine derivative or the salt thereof according to (22), wherein Y in Formula 2 is an oxygen atom. (24) The triazine derivative or the salt thereof according to (22) or (23), wherein R¹ in Formula 2 represents a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone). (25) The triazine derivative or the salt thereof according to any one of (22) to (24), wherein R² in Formula 2 represents a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α). (26) The triazine derivative or the salt thereof according to (22) or (23), wherein B is a hydroxyl group and R² is a C₁-C₆ alkyl group. (27) The triazine derivative or the salt thereof according to (26), wherein R¹ represents a group selected from a group consisting of a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆. alkylidene aminooxy C₁-C₆ alkyl group; a NR³¹R³² group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone]. (28) The triazine derivative or the salt thereof according to (26), wherein R¹ represents a group selected from a group consisting of a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a NR³¹R³² group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone]. (29) The triazine derivative or the salt thereof according to (27) or (28), wherein a heterocyclic group is 5- or 6-membered aromatic heterocyclic group having 1 to 3 nitrogen atoms as a heteroatom. (30) The triazine derivative or the salt thereof according to any one of (26) to (29), wherein R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a benzyl group which may be substituted with one or more substituents selected from the Substituent group α; a C₁-C₆ alkylcarbonyl group; a C₁-C₆ alkoxycarbonyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; or R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and in such case, one or more carbon atom in the ring may be substituted with a sulfur atom and/or an oxygen atom. (31) The triazine derivative or the salt thereof according to (30), wherein R³¹ and R³² each independently represent a hydrogen atom; a C₁-C₆ alkyl group; or a phenyl group which may be substituted with one or more substituents selected from the Substituent group α. (32) The triazine derivative or the salt thereof according to any one of (26) to (31), wherein “Substituent group α” represents a group selected from a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ haloalkylthio group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; or a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group. (33) The triazine derivative or the salt thereof according to (32), wherein “Substituent group α” represents a group selected from a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; or a C₁-C₆ alkylthio group. (34) The triazine derivative or the salt thereof according to any one of (22) to (33), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone); and

R² in Formula 2 represents a group selected from a group consisting of a C₁-C₆a alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α).

(35) The triazine derivative or the salt thereof according to any one of (22) to (34), wherein

Y in Formula 2 is an oxygen atom,

R¹ in Formula 2 represents a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the Substituent group α; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and piperazinyl group (the group may be substituted with 1 to 5 identical or different substituents selected from the Substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone);

R² is a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; and a pyridyl group; and,

“Substituent group α” represents a group selected from a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.

(36) An agrochemical composition comprising the triazine derivative or the salt thereof described in any one of (22) to (35), and an agriculturally acceptable carrier. (37) The agrochemical composition according to (36), in which the agrochemical composition further comprises a surface active agent. (38) A herbicide comprising the triazine derivative or the salt thereof described in any one of (22) to (35) as an active component. (39) The herbicide according to (38), in which the herbicide has a herbicidal activity for weeds in a field or a paddy field in which agrohorticultural plants are cultivated. (40) The herbicide according to (39), in which the agrohorticultural plants are agrohorticultural plants given with resistance by a breeding method or a genetic recombination technique. (41) A method of eliminating weeds in soils by applying an effective amount of herbicides comprising the triazine derivative or the salt thereof described in any one of (22) to (35). (42) The method according to (41), in which the soils are a farmland. (43) The method according to (41), in which the farmland is a field or a paddy field in which agrohorticultural plants are cultivated.

Advantageous Effects of Invention

The invention provides the novel triazine derivative represented by Formula 1 or its salt which can effectively control weeds. The triazine derivative of the invention or its salt exhibits an excellent herbicidal effect against various weeds, which cause a problem particularly in an agricultural field over a long period of time from a pre-germination stage to a growing stage, for example, a broad-leaf weed like white pepper, Amaranthus viridis, white goosefoot, Stellaria media, chamomile, China jute, Sida spinosa, sesbania, hogweed, red poppy, morning glory, and cocklebur, annual and perennial weeds of Cyperus microiria family including coco grass, edible galingale, Kyllinga brevifolia var. leiolepis, java galingale, and Cyperus iria, and gramineous weeds like barnyard millet, finger grass, foxtail, spear grass, Syrian sorghum nitidum, short awn, and wild oat. In addition, it can control rice paddy weeds including annual weeds like Echinochloa oryzicola, Cyperus difformis, and Monochoria vaginalis and perennial weeds like Sagittaria pygmaea, Sagittaria trifolia, Cyperus serotinus, Eleocharis kuroguwai, Scirpus hotarui, and Alisma canaliculaturn.

Further, the compound of the invention is highly safe to useful crops and useful plants, in particular, to rice, wheat, barley, corn, grain sorghum, soybean, cotton, sugar beet, etc.

Thus, the invention provides an agrochemical composition having an excellent effect as herbicides.

DESCRIPTION OF EMBODIMENTS

The definitions of the terms used in the present Description are given below.

Halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

The descriptions like C₁-C₆ indicate the number of carbon atoms in a substituent group described hereinbelow. For example, C₁-C₆ means 1 to 6 carbon atoms.

The C₁-C₆ alkyl group represents, unless specified otherwise, a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include a group like methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

The C₁-C₁₂ alkyl group represents, unless specified otherwise, a linear or branched alkyl group having 1 to 12 carbon atoms, and examples thereof include, in addition to those exemplified above for the C₁-C₆ alkyl group, a group like heptyl, 1-methylhexyl, 5-methylhexyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 4,4-dimethylpentyl, 1-ethylpentyl, 2-ethylpentyl, 1,1,3-trimethylbutyl, 1,2,2-trimethylbutyl, 1,3,3-trimethylbutyl, 2,2,3-trimethylbutyl, 2,3,3-trimethylbutyl, 1-propylbutyl, 1,1,2,2-tetramethylpropyl, octyl, 1-methylheptyl, 3-methylheptyl, 6-methylheptyl, 2-ethylhexyl, 5,5-dimethylhexyl, 2,4,4-trimethylpentyl, 1-ethyl-1-methylpentyl, nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 7-methyloctyl, 1-ethylheptyl, 1,1-dimethylheptyl, 6,6-dimethylheptyl, decyl, 1-methylnonyl, 2-methylnonyl, 6-methylnonyl, 1-ethyloctyl, 1-propylheptyl, n-nonyl, and n-decyl.

The C₃-C₆ cycloalkyl group represents, unless specified otherwise, a cycloalkyl group having 3 to 6 carbon atoms, and examples thereof include a group like cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

The C₃-C₆ cycloalkenyl group represents, unless specified otherwise, a cycloalkenyl group having 3 to 6 carbon atoms, and examples thereof include a group like cyclopentenyl and cyclohexenyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a cycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl, 1-cyclopropylpropyl, 2-cyclopropylpropyl, 3-cyclopropylpropyl, cyclobutylmethyl, cyclopentylmethyl, and cyclohexylmethyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group represents an (alkyl)-O— group (i.e., alkoxy group) having 1 to 6 carbon atoms substituted with a cycloalkyl having 3 to 6 carbon atoms, wherein the cycloalkyl moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethoxy, 1-cyclopropylethoxy, 2-cyclopropylethoxy, 1-cyclopropylpropoxy, 2-cyclopropylpropoxy, 3-cyclopropylpropoxy, cyclobutylmethoxy, cyclopentylmethoxy, and cyclohexylmethoxy.

The C₃-C₆ halocycloalkyl group represents, unless specified otherwise, a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, or preferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety and the halogen atom have the same definitions as above, and examples thereof include a group like 2,2-difluorocyclopropyl and 2,2-dichlorocyclopropyl.

The C₃-C₆ halocycloalkyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a cycloalkyl group having 3 to 6 carbon atoms substituted with 1 to 5, or preferably 1 to 3 halogen atoms, wherein the cycloalkyl moiety, the alkyl moiety, and the halogen atom have the same definitions as above, and examples thereof include a group like 2,2-difluorocyclopropylmethyl and 2,2-dichlorocyclopropylmethyl.

The amino C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an amino group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-aminoethyl and 3-aminopropyl.

The nitro C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a nitro group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like nitromethyl and 2-nitroethyl.

The C₁-C₆ haloalkyl group represents a linear or branched alkyl group having 1 to 6 carbon atoms substituted with a halogen atom, and examples thereof include a group like fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, bromodifluoromethyl, 2-fluoroethyl, 1-chloroethyl, 2-chloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2-difluoroethyl, 1,2-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2-bromo-2-chloroethyl, 2-chloro-1,1,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 2-bromopropyl, 3-bromopropyl, 2-bromo-1-methylethyl, 3-iodopropyl, 2,3-dichloropropyl, 2,3-dibromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 3-bromo-3,3-difluoropropyl, 3,3-dichloro-3-fluoropropyl, 2,2,3,3-tetrafluoropropyl, 1-bromo-3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, heptafluoropropyl, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl, 2,3-dichloro-1,1,2,3,3-pentafluoropropyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 2-chloro-1,1-dimethylethyl, 4-bromobutyl, 3-bromo-2-methylpropyl, 2-bromo-1,1-dimethylethyl, 2,2-dichloro-1,1-dimethylethyl, 2-chloro-1-chloromethyl-2-methylethyl, 4,4,4-trifluorobutyl, 3,3,3-trifluoro-1-methylpropyl, 3,3,3-trifluoro-2-methylpropyl, 2,3,4-trichlorobutyl, 2,2,2-trichloro-1,1-dimethylethyl, 4-chloro-4,4-difluorobutyl, 4,4-dichloro-4-fluorobutyl, 4-bromo-4,4-difluorobutyl, 2,4-dibromo-4,4-difluorobutyl, 3,4-dichloro-3,4,4-trifluorobutyl, 3,3-dichloro-4,4,4-trifluorobutyl, 4-bromo-3,3,4,4-tetrafluorobutyl, 4-bromo-3-chloro-3,4,4-trifluorobutyl, 2,2,3,3,4,4-hexafluorobutyl, 2,2,3,4,4,4-hexafluorobutyl, 2,2,2-trifluoro-1-methyl-1-trifluoromethylethyl, 3,3,3-trifluoro-2-trifluoromethylpropyl, 2,2,3,3,4,4,4-heptafluorobutyl, 2,3,3,3-tetrafluoro-2-trifluoromethylpropyl, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 5-fluoropentyl, 5-chloropentyl, 5,5-difluoropentyl, 5,5-dichloropentyl, 5,5,5-trifluoropentyl, 6,6,6-trifluorohexyl, and 5,5,5,6,6,6-pentafluorohexyl.

The C₂-C₆ alkenyl group represents, unless specified otherwise, a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include a group like vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 1-methyl-1-propenyl, 2-butenyl, 1-methyl-2-propenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-ethyl-2-propenyl, 2-pentenyl, 1-methyl-1-butenyl, 3-pentenyl, 1-methyl-2-butenyl, 4-pentenyl, 1-methyl-3-butenyl, 3-methyl-1-butenyl, 1,2-dimethyl-2-propenyl, 1,1-dimethyl-2-propenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1,2-dimethyl-1-propenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,3-pentadienyl, 1-vinyl-2-propenyl, 1-hexenyl, 1-propyl-2-propenyl, 2-hexenyl, 1-methyl-1-pentenyl, 1-ethyl-2-butenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-4-pentenyl, 1-ethyl-3-butenyl, 1-(isobutyl)vinyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-(isopropyl)-2-propenyl, 2-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1,3-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1,5-hexadienyl, 1-vinyl-3-butenyl, and 2,4-hexadienyl.

The C₂-C₆ alkynyl group represents, unless specified otherwise, a linear or branched alkynyl group having 2 to 6 carbon atoms, and examples thereof include a group like ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-(n-propyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

The C₂-C₆ halolalkenyl group represents, unless specified otherwise, a linear or branched alkenyl group having 2 to 6 carbon atoms substituted with 1 to 11 halogen atoms that are the same or different from each other, and examples thereof include 2-chlorovinyl, 2-bromovinyl, 2-iodovinyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 1-chloromethylvinyl, 2-bromo-1-methylvinyl, 1-trifluoromethylvinyl, 3,3,3-trichloro-1-propenyl, 3-bromo-3,3-difluoro-1-propenyl, 2,3,3,3-tetrachloro-1-propenyl, 1-trifluoromethyl-2,2-difluorovinyl, 2-chloro-2-propenyl, 3,3-difluoro-2-propenyl, 2,3,3-trichloro-2-propenyl, 4-bromo-3-chloro-3,4,4-trifluoro-1-butenyl, 1-bromomethyl-2-propenyl, 3-chloro-2-butenyl, 4,4,4-trifluoro-2-butenyl, 4-bromo-4,4-difluoro-2-butenyl, 3-bromo-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3,4,4-tribromo-3-butenyl, 3-bromo-2-methyl-2-propenyl, 3,3-difluoro-2-methyl-2-propenyl, 3,3,3-trifluoro-2-methylpropenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, 3,3,3-trifluoro-1-methyl-1-propenyl, 3,4,4-trifluoro-1,3-butadienyl, 3,4-dibromo-1-pentenyl, 4,4-difluoro-3-methyl-3-butenyl, 3,3,4,4,5,5,5-heptafluoro-1-pentenyl, 5,5-difluoro-4-pentenyl, 4,5,5-trifluoro-4-pentenyl, 3,4,4,4-tetrafluoro-3-trifluoromethyl-1-butenyl, 4,4,4-trifluoromethyl-3-methyl-2-butenyl, 3,5,5-trifluoro-2,4-pentadienyl, 4,4,5,5,6,6,6-heptafluoro-2-hexenyl, 3,4,4,5,5,5-hexafluoro-3-trifluoromethyl-1-pentenyl, 4,5,5,5-tetrafluoro-4-trifluoromethyl-2-pentenyl, and 5-bromo-4,5,5-trifluoro-4-trifluoromethyl-2-pentenyl.

The C₂-C₆ halolalkynyl group represents, unless specified otherwise, a linear or branched alkynyl group having 2 to 6 carbon atoms substituted with 1 to 9 halogen atoms that are the same or different from each other, and examples thereof include 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl, 3-chloro-1-propynyl, and 5-chloro-4-pentynyl.

The C₁-C₆ alkoxy group represents an (alkyl)-O— group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, and hexyloxy.

The C₁-C₆ haloalkoxy group represents a linear or branched alkyl-O— group having 1 to 6 carbon atoms substituted with 1 to 13 halogen atoms that are the same or different from each other, wherein the haloalkyl moiety has the same definition as above, and examples thereof include a group like chloromethoxy, difluoromethoxy, chlorodifluoromethoxy, trifluoromethoxy, and 2,2,2-trifluoroethoxy.

The C₁-C₆ alkoxy C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like methoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl, methoxyethyl, and butoxyethyl.

The hydroxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a hydroxy group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-hydroxyethyl and 3-hydroxypropyl.

The C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like 2-(2-methoxyethoxy)ethyl and 2-(2-ethoxyethoxy)ethyl.

The phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a phenyl, wherein the alkyl moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like benzyloxymethyl and benzyloxyethyl.

The C₁-C₆ haloalkoxy C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a haloalkoxy group having 1 to 6 carbon atoms, wherein the haloalkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like chloromethoxymethyl, difluoromethoxymethyl, chlorodifluoromethoxymethyl, trifluoromethoxymethyl, and 2,2,2-trifluoroethoxymethyl.

The C₁-C₆ haloalkoxy C₁-C₆ alkoxy group represents, unless specified otherwise, an alkoxy group having 1 to 6 carbon atoms substituted with a haloalkoxy group having 1 to 6 carbon atoms, wherein the haloalkoxy moiety and alkoxy moiety have the same definitions as above, and examples thereof include a group like chloromethoxymethoxy, difluoromethoxymethoxy, chlorodifluoromethoxymethoxy, trifluoromethoxymethoxy, and 2,2,2-trifluoroethoxymethoxy.

The C₃-C₆ cycloalkyloxy group represents, unless specified otherwise, a (cycloalkyl)-O— group having 3 to 6 carbon atoms, wherein the cycloalkyl moiety has the same definition as above, and examples thereof include a group like cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy.

The C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a (cycloalkyl)-O— group having 3 to 6 carbon atoms, wherein the alkyl moiety and cycloalkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropyloxymethyl, cyclobutyloxymethyl, cyclopentyloxymethyl, and cyclohexyloxymethyl.

The C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a cycloalkyl group having 3 to 6 carbon atoms, wherein the alkyl moiety, alkoxy moiety, and cycloalkyl moiety have the same definitions as above, and examples thereof include a group like cyclopropylmethyloxymethyl, cyclobutylmethyloxymethyl, cyclopentylmethyloxymethyl, and cyclohexylmethyloxymethyl.

The (R³¹R³²N—C═O) C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (R³¹R³²N—OC—) group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like N,N-dimethylaminocarbonylmethyl, N,N-dimethylaminocarbonylethyl, and N-methyl-N-ethylaminocarbonylmethyl.

The C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methoxy-2-oxoethyl, 2-ethoxy-2-oxoethyl, and 2-tert-butoxy-2-oxoethyl.

The C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group represents, unless specified otherwise, an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxycarbonyl group having 1 to 6 carbon atoms, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like a 2-methoxy-2-oxoethoxy group, a 2-ethoxy-2-oxoethoxy group, and a 2-tert-butoxy-2-oxoethoxy group.

The C₁-C₆ alkylcarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include acetyl and propionyl.

The C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkylcarbonyl group having 1 to 6 carbon atoms, wherein the alkylcarbonyl moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-oxopropyl, 3-oxopropyl, and 2-oxobutyl.

The C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an (alkyl (having 1 to 6 carbon atoms))-C(═O)O— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like acetoxymethyl, propionyloxymethyl, isopropionyloxymethyl, and pivaloyloxymethyl.

The C₁-C₆ alkylidene group represents, unless specified otherwise, a divalent alkylidene group having 1 to 6 carbon atoms, wherein a single carbon carries a divalent charge and the alkyl moiety has the same definition as above, and examples thereof include a group like a methylene group, an ethylidene group, and an isopropylidene group.

The C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with (alkylidene (having 1 to 6 carbon atoms))=N—O—, wherein the alkylidene moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like methyleneaminooxymethyl, 2-(ethylidene aminooxy)ethyl, and 2-(isopropylidene aminooxy)ethyl.

The C₂-C₆ alkenyloxy group represents, unless specified otherwise, an (alkenyl)-O— group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like 2-propenyloxy.

The C₂-C₆ alkynyloxy group represents, unless specified otherwise, an (alkynyl)-O— group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include 2-propynyloxy.

The phenyloxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-O— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenoxymethyl, 2-phenoxyethyl, and 3-phenoxypropyl.

The phenylthio C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-S— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenylthiomethyl, 2-phenylthioethyl, and 3-phenylthiopropyl.

The phenylsulfinyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-SO— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like phenylsulfinylmethyl, 2-phenylsulfinylethyl, and 3-phenylsulfinylpropyl.

The phenylsulfonyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (phenyl)-SO₂— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like 2-phenylsulfonylethyl, 3-phenylsulfonylpropyl, and 4-phenylsulfonylbutyl.

The C₁-C₆ alkoxyimino group represents, unless specified otherwise, an (alkoxy)-N═ group having 1 to 6 carbon atoms, wherein the alkoxy moiety has the same definition as above, and examples thereof include methoxyimino and ethoxyimino.

The C₁-C₆ alkoxyimino C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxyimino group having 1 to 6 carbon atoms, wherein the alkoxyimino moiety and alkyl moiety have the same definitions as above, and examples thereof include methoxyiminomethyl and ethoxyiminomethyl.

The phenoxyimino group represents, unless specified otherwise, a (substituted) (phenoxy)-N═ group, and examples thereof include phenoxyimino.

The phenoxyimino C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a phenoxyimino group, wherein the phenoxyimino moiety and alkyl moiety have the same definitions as above, and examples thereof include phenoxyiminomethyl.

The di(C₁-C₆ alkoxy) C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms di-substituted with an alkoxy group having 1 to 6 carbon atoms, and examples thereof include (2,2-dimethoxy)ethyl, (3,3-dimethoxy)propyl, (2,2-diethoxy)ethyl group, and a (3,3-diethoxy)propyl.

The formyl C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with a formyl group, wherein the alkyl moiety has the same definition as above, and examples thereof include (2-formyl)ethyl and (3-formyl)propyl.

The C₁-C₆ alkylthio group represents an (alkyl)-S— group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylthio, ethylthio, n-propylthio, and isopropylthio.

The C₁-C₁₀ alkylthio group represents an (alkyl)-S— group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the C₁-C₆ alkylthio group, n-heptylthio, n-octylthio, n-nonylthio, and n-decylthio.

The C₁-C₆ alkylsulfinyl group represents an (alkyl)-SO— group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, and isopropylsulfinyl.

The C₁-C₁₀ alkylsulfinyl group represents an (alkyl)-S— group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the C₁-C₆ alkylsulfinyl group, n-heptylsulfinyl, n-octylsulfinyl, n-nonylsulfinyl, and n-decylsulflinyl.

The C₁-C₆ alkylsulfonyl group represents an (alkyl)-SO₂— group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, and isopropylsulfonyl.

The C₁-C₁₀ alkylsulfonyl group represents an (alkyl)-SO₂— group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include, in addition to those exemplified above for the C₁-C₆ alkylsulfonyl group, n-heptylsulfonyl, n-octylsulfonyl, n-nonylsulfonyl, and n-decylsulfonyl.

The C₂-C₆ alkenylthio group represents an (alkenyl)-S— group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylthio.

The C₂-C₆ alkenylsulfinyl group represents an (alkenyl)-SO— group having 3 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylsulfinyl.

The C₂-C₆ alkenylsulfonyl group represents an (alkenyl)-SO₂— group having 2 to 6 carbon atoms, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like allylsulfonyl.

The C₂-C₆ alkynylthio group represents an (alkynyl)-S— group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylthio.

The C₂-C₆ alkynylsulfinyl group represents an (alkynyl)-SO— group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylsulfinyl.

The C₂-C₆ alkenylsulfonyl group represents an (alkynyl)-SO₂— group having 2 to 6 carbon atoms, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 2-propynylsulfonyl.

The C₁-C₁₀ alkylsulfonyloxy group represents an (alkyl)SO₂—O— group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylsulfonyloxy and ethylsulfonyloxy.

The C₁-C₆ alkylthio C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylthio group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkylthio moiety have the same definitions as above, and examples thereof include methylthiomethyl and ethylthiomethyl.

The C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylsulfinyl group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkylsulfinyl moiety have the same definitions as above, and examples thereof include methylsulfinylmethyl and ethylsulfinylmethyl.

The C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylsulfonyl group having 1 to 6 carbon atoms, wherein the alkyl moiety and alkylsulfonyl moiety have the same definitions as above, and examples thereof include methylsulfonylmethyl and ethylsulfonylmethyl.

The C₁-C₆ alkoxy C₁-C₆ alkoxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with an alkoxy having 1 to 6 carbon atoms, wherein the alkoxy moiety has the same definition as above, and examples thereof include a group like methoxymethoxy, ethoxymethoxy, 2-methoxyethoxy, and 2-ethoxyethoxy.

The C₁-C₆ haloalkylthio C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (haloalkyl)-S— group having 1 to 6 carbon atoms, wherein the alkyl moiety and haloalkyl moiety have the same definitions as above, and examples thereof include a group like difluoromethylthiomethyl and trifluoromethylthiomethyl.

The C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (haloalkyl)-SO— group having 1 to 6 carbon atoms, wherein the alkyl moiety and haloalkyl moiety have the same definitions as above, and examples thereof include a group like difluoromethylsulfinylmethyl and trifluoromethylsulfinylmethyl.

The C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with a (haloalkyl)-SO₂— group having 1 to 6 carbon atoms, wherein the alkyl moiety and haloalkyl moiety have the same definitions as above, and examples thereof include a group like difluoromethylsulfonylmethyl and trifluoromethylsulfonylmethyl.

The C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkylthio group having 1 to 6 carbon atoms, wherein the alkylthio moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylthioethoxymethyl and 2-ethylthioethoxymethyl.

The C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkynylsulfinyl group having 1 to 6 carbon atoms, wherein the alkynylsulfinyl moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylsulfinyl ethoxymethyl and 2-ethylsulfinyl ethoxymethyl.

The C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with an alkynylsulfonyl group having 1 to 6 carbon atoms, wherein the alkylsulfonyl moiety, alkoxy moiety, and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-methylsulfonylethoxymethyl and 2-ethylsulfonylethoxymethyl.

The C₁-C₆ acyl group represents an acyl group derived from C₁-C₆ carboxylic acid, and examples thereof include an acetyl group and a propionyl group.

The C₁-C₆ alkylcarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include an acetyl group and a propionyl group.

The C₁-C₆ alkylcarbonyloxy group represents an (alkyl (having 1 to 6 carbon atoms))-C(═O)—O— group, wherein the alkyl moiety has the same definition as above, and examples thereof include acetoxy and propionyloxy.

The C₁-C₆ haloalkylcarbonyloxy group represents a (haloalkyl (having 1 to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include a group like chloromethylcarbonyloxy, difluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, trifluoromethylcarbonyloxy, and 2,2,2-trifluoroethylcarbonyloxy.

The C₂-C₆ alkenylcarbonyloxy group represents an (alkenyl (having 2 to 6 carbon atoms))-C(═O)—O— group, wherein the alkenyl moiety has the same definition as above, and examples thereof include a group like 1-propenylcarbonyloxy, 2-propenylcarbonyloxy, 1-butenylearbonyloxy, and 1-methyl-1-propenylcarbonyloxy.

The C₂-C₆ halolalkenylcarbonyloxy group represents a (haloalkenyl (having 2 to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkenyl moiety has the same definition as above, and examples thereof include a group like 3-chloro-2-propenylcarbonyloxy and 3-bromo-2-propenylcarbonyloxy.

The C₂-C₆ alkynylcarbonyloxy group represents an (alkynyl (having 2 to 6 carbon atoms))-C(═O)—O— group, wherein the alkynyl moiety has the same definition as above, and examples thereof include a group like 1-propynylcarbonyloxy and 2-propynylcarbonyloxy.

The C₂-C₆ haloalkynylcarbonyloxy group represents a (haloalkynyl (having 2 to 6 carbon atoms))-C(═O)—O— group, wherein the haloalkynyl moiety has the same definition as above, and examples thereof include a group like 3-chloro-1-propynylcarbonyloxy and 3,3,3-trifluoro-1-propynylcarbonyloxy.

The C₂-C₆ alkylidene amino group represents an alkyl (having 1 to 5 carbon atoms)-CH═N— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like ethylideneamino and propylideneamino.

The di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group represents an amino group substituted with an alkylidene group having 1 to 6 carbon atoms substituted with an amino group di-substituted with an alkyl group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like a dimethylamino methylidene amino group and a diethylamino methylidene amino group.

The C₁-C₁₀ alkylamino group represents an (alkyl)-NH— group having 1 to 10 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include methylamino and ethylamino.

The di(C₁-C₁₀ alkyl)amino group represents an (alkyl)₂N— group, wherein the alkyl moiety has the same definition as above, and examples thereof include dimethylamino, diethylamino, methylethylamino, dipropylamino, and dibutylamino.

The mono(C₁-C₆ alkyl)amino group represents an (alkyl)-NH— group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like methylamino and ethylamino.

The di(C₁-C₆ alkyl)amino group represents an (alkyl (having 1 to 6 carbon atoms))₂N— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like dimethylamino, diethylamino, methylethylamino, dipropylamino, and dibutylamino.

The C₁-C₆ alkylamino C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an alkylamino group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include N-methylaminomethyl and N-methylaminoethyl.

The di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group represents an alkyl group having 1 to 6 carbon atoms substituted with an (alkyl (having 1 to 6 carbon atoms))₂N— group, wherein the alkyl moiety has the same definition as above, and examples thereof include N,N-dimethylaminomethyl and N,N-dimethylaminoethyl.

The C₁-C₆ alkoxycarbonyl amino group represents an amino group substituted with an (alkoxy (having 1 to 6 carbon atoms))-C(═O)— group, wherein the alkoxy moiety has the same definition as above, and examples thereof include methoxycarbonyl amino and ethoxycarbonyl amino.

The C₁-C₆ alkylcarbonyl amino group represents, unless specified otherwise, an amino group substituted with an alkylacarbonyl group having 1 to 6 carbon atoms, wherein the alkylcarbonyl moiety has the same definition as above, and examples thereof include a group like formamide, acetamide, and propionamide.

The C₁-C₆ alkoxycarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-O—C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, and isopropoxycarbonyl.

The C₁-C₁₀ alkylthiocarbonyl group represents an (alkyl (having 1 to 10 carbon atoms))-S—C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include methylthiocarbonyl and ethylthiocarbonyl.

The C₁-C₆ alkoxycarbonyloxy group represents an oxy group substituted with an (alkoxy (having 1 to 6 carbon atoms))-C(═O)— group, wherein the alkoxycarbonyl moiety has the same definition as above, and examples thereof include methoxycarbonyloxy and ethoxycarbonyloxy.

The C₁-C₆ haloalkylcarbonyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-C(═O)— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include chloroacetyl, trifluoroacetyl, pentafluoropropionyl, and difluoromethylthio.

The C₁-C₆ haloalkylthio group represents a (haloalkyl (having 1 to 6 carbon atoms))-S— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include difluoromethylthio and trifluoromethylthio.

The C₁-C₆ haloalkylsulfinyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-SO— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include trifluoromethylsulfinyl and difluoromethylsulfinyl.

The C₁-C₆ haloalkylsulfonyl group represents a (haloalkyl (having 1 to 6 carbon atoms))-SO₂— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include chloromethylsulfonyl, difluoromethylsulfonyl, and trifluoromethylsulfonyl.

The C₁-C₆ haloalkylsulfonyloxy group represents a (haloalkyl (having 1 to 6 carbon atoms))-SO₂—O— group, wherein the haloalkyl moiety has the same definition as above, and examples thereof include chloromethylsulfonyloxy and trifluoromethylsulfonyloxy.

The mono(C₁-C₆ alkyl)aminocarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))-NH—C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include methylaminocarbonyl and ethylaminocarbonyl.

The di(C₁-C₆ alkyl)aminocarbonyl group represents an (alkyl (having 1 to 6 carbon atoms))₂N—C(═O)— group, wherein the alkyl moiety has the same definition as above, and examples thereof include a group like dimethylaminocarbonyl, diethylaminocarbonyl, methylethylaminocarbonyl, dipropylaminocarbonyl, and dibutylaminocarbonyl.

The cyano C₁-C₆ alkyl group represents a cyano alkyl group having 1 to 6 carbon atoms, wherein the alkyl moiety has the same definition as above, and examples thereof include cyanomethyl and cyanoethyl.

The cyano C₁-C₆ alkoxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with a cyano group, wherein the alkoxy moiety has the same definition as above, and examples thereof include a group like 2-cyanoethoxy and 3-cyanopropoxy.

The cyano C₁-C₆ alkoxy C₁-C₆ alkyl group represents, unless specified otherwise, an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a cyano group, wherein the alkoxy moiety and alkyl moiety have the same definitions as above, and examples thereof include a group like 2-cyanoethoxymethyl and 3-cyanopropoxymethyl.

The phenyl C₁-C₆ alkyl group represents an alkyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkyl moiety has the same definition as above, and examples thereof include benzyl, phenethyl, and phenylpropyl.

The phenyl C₂-C₆ alkenyl group represents an alkenyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkenyl moiety has the same definition as above, and examples thereof include styryl and cinnamyl.

The phenyl C₂-C₆ alkynyl group represents an alkynyl group having 2 to 6 carbon atoms substituted with a phenyl group, wherein the alkynyl moiety has the same definition as above, and examples thereof include (2-phenyl)ethynyl and 2-(3-phenyl)ethynyl.

The phenylcarbonyloxy group represents a (phenyl)-C(═O)—O— group and examples thereof include a phenylcarbonyloxy group.

The phenylcarbonyl C₁-C₆ alkyloxy group represents an alkoxy group having 1 to 6 carbon atoms substituted with a (phenyl)-C(═O)group and examples thereof include phenylcarbonylmethoxy.

The phenylthio group represents a phenyl-S— group.

The phenylsulfinyl group represents a phenyl-SO— group.

The phenylsulfonyl group represents a phenyl-SO₂— group.

The phenylsulfonyloxy group represents a phenyl-SO₂—O— group.

The benzylthio group represents a benzyl-S— group.

The benzylsulfinyl group represents a benzyl-SO— group.

The benzylsulfonyl group represents a benzyl-SO₂— group.

The benzylsulfonyloxy group represents a benzyl-SO₂—O— group.

As a group constituting a C₃-C₆ alkylene group, 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting a carbonyl group, and the C₃-C₆ alkylene group is a linear or branched divalent alkylene group having 3 to 6 carbon atoms, and 1 to 3 carbon atoms in the alkylene group may be substituted with an atom or a group of atoms selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting a carbonyl group, and examples thereof include a trimethylene group, a propylene group, a butylene group, a methylenedioxy group, and an ethylenedioxy group. Preferred examples of the alkylene group include a C₁-C₃ alkylenedioxy group.

Examples of the heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom include furan, thiophene, pyrrole, pyrazole, imidazole, pyridine, pyrimidine, pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, morpholine, thiomorpholine, benzofuran, benzothiophene, indole, benzoxazole, benzothiazole, benzimidazole, isoxazole, isoxazoline, oxazole, oxazoline, isothiazole, isothiazoline, thiazole, tetrahydrofuran, and thiazoline. Preferred examples of the heterocyclic group include pyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole, morpholine, thiomorpholine (sulfur atom of thiomorpholine may be bonded with one or two oxygen atoms), piperidine, pyridazine, piperazine, and tetrahydrofuran. More preferred examples of the heterocyclic group include pyridine, pyrimidine, pyrazine, thiophene, pyrazole, isoxazole, morpholine, thiomorpholine (sulfur atom of thiomorpholine may be bonded with one or two oxygen atoms), and piperidine.

The heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and optionally selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents, unless specified otherwise, a group in which the oxygen atom is substituted with a heterocycle having the same definition as above, and examples thereof include (tetrahydrofuran-2-yl)oxy, (4,5-dihydroisoxazol-5-yl)oxy, (isoxazol-5-yl)oxy, and a (thiophen-2-yl)oxy group.

The C₁-C₆ alkyl group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with a heterocycle wherein the alkyl moiety and heterocyclic moiety have the same definitions as above, and examples thereof include (2-furan)methyl, (3-furan)methyl, (2-thiophene)methyl, and (3-thiophene)methyl.

The C₁-C₆ alkyl group substituted with a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with a heterocyclic oxy group wherein the alkyl moiety and heterocyclic moiety have the same definitions as above, and examples thereof include (tetrahydrofuran-2-yl)oxymethyl, (4,5-dihydroisoxazol-5-yl)oxymethyl, (isoxazol-5-yl)oxymethyl, and (thiophen-2-yl)oxymethyl.

The C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic oxy group wherein the alkyl moiety, alkoxy moiety, and heterocyclic moiety have the same definitions as above, and examples thereof include (tetrahydrofuran-2-yl)oxymethoxymethyl, (4,5-dihydroisoxazol-5-yl)oxyethoxymethyl, (isoxazol-5-yl)oxymethoxymethyl, and (thiophen-2-yl)oxyethoxymethyl.

The C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkyl group having 1 to 6 carbon atoms substituted with an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic group wherein the alkyl moiety, alkoxy moiety, and heterocyclic moiety have the same definitions as above, and examples thereof include tetrahydrofurfuryloxyethyl and tetrahydrofurfuryloxymethyl.

The C₁-C₆ alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom represents an alkoxy group having 1 to 6 carbon atoms substituted with a heterocyclic group wherein the heterocyclic moiety and alkoxy moiety have the same definitions as above, and examples thereof include a 6-methyl-2-pyridinemethoxy group and a tetrahydrofurfuryloxy group.

Alkali metal includes sodium, potassium, and the like.

Next, specific examples of the compound of the invention represented by Formula 1 are described in Table 1 to Table 43. However, the invention is not limited to those compounds.

In the present Description, the following descriptions included in the tables indicate the corresponding group, respectively, as shown below.

For example, Me represents a methyl group, Et represents an ethyl group, Pr-n represents a n-propyl group, Pr-i represents an isopropyl group, Pr-c represents a cyclopropyl group, Bu-n represents a n-butyl group, Bu-s represents a secondary butyl group, Bu-i represents an isobutyl group, Bu-t represents a tertiary butyl group, Bu-c represents a cyclobutyl group, Pen-n represents a n-pentyl group, Pen-c represents a cyclopentyl group, Hex-n represents a n-hexyl group, Hex-c represents a cyclohexyl group, Ac represents an acetyl group, Ph represents a phenyl group, Bn represents a benzyl group, Ts represents a p-toluene sulfonyl group, pyridyl represents a pyridyl group, and pyrimidinyl represents a pyrimidinyl group. Further, Ph(2-OMe) represents a 2-methoxyphenyl group, CH₂Ph(2-OMe) represents a 2-methoxybenzyl group, and Ph(3,4-Cl₂) represents a 3,4-dichlorophenyl group.

TABLE 1

Compound No. R¹ R² Y Z R⁴ I-1  Me Me O O OH I-2  Et Me O O OH I-3  Pr-n Me O O OH I-4  Pr-i Me O O OH I-5  Bu-n Me O O OH I-6  Bu-i Me O O OH I-7  Bu-s Me O O OH I-8  Bu-t Me O O OH I-9  Hex-n Me O O OH I-10 CH₂CF₃ Me O O OH I-11 CH₂CH═CH₂ Me O O OH I-12 CH₂C(Me)═CH₂ Me O O OH I-13 CH₂CH₂CH═OMe₂ Me O O OH I-14 CH₂C≡CH Me O O OH I-15 CH₂C≡CCH₃ Me O O OH I-16 Pr-c Me O O OH I-17 Bu-c Me O O OH I-18 Pen-c Me O O OH I-19 Hex-c Me O O OH I-20 CH₂Pr-c Me O O OH I-21 CH₂Bu-c Me O O OH I-22 CH₂Pen-c Me O O OH I-23 CH₂Hex-c Me O O OH I-24 CH₂CH═CCl₂ Me O O OH I-25 CH₂CCl═CHCl Me O O OH I-26 CH₂CH₂CH═CCl₂ Me O O OH I-27 CH₂CH₂C(Me)═CF₂ Me O O OH I-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O OH I-29 CH₂CH═CF₂ Me O O OH I-30 CH₂CH₂OMe Me O O OH I-31 CH₂CH₂OEt Me O O OH I-32 CH(Me)CH₂OMe Me O O OH I-33 CH₂CH₂OCH₂CH₂OMe Me O O OH I-34 CH₂CH₂OPr-n Me O O OH I-35 CH₂CH₂OPr-i Me O O OH I-36 CH₂CH₂OPr-c Me O O OH I-37 CH₂CH₂OBu-c Me O O OH I-38 CH₂CH₂OPen-c Me O O OH I-39 CH₂CH₂OHex-c Me O O OH I-40 CH₂CH₂OCH₂CF₃ Me O O OH I-41 CH₂CH₂CH₂OMe Me O O OH

TABLE 2 Compound No. R¹ R² Y Z R⁴ I-42 CH═CHMe Me O O OH I-43 CH₂SMe Me O O OH I-44 CH₂SPr-n Me O O OH I-45 CH₂CH₂SMe Me O O OH I-46 CH₂SOMe Me O O OH I-47 CH₂SO₂Me Me O O OH I-48 CH₂CH₂CH₂SMe Me O O OH I-49 CH₂CH₂CH₂SO₂Me Me O O OH I-50 Ph Me O O OH I-51 Ph(2-Cl) Me O O OH I-52 Ph(3-Cl) Me O O OH I-53 Ph(4-Cl) Me O O OH I-54 Ph(2-F) Me O O OH I-55 Ph(3-F) Me O O OH I-56 Ph(4-F) Me O O OH I-57 Ph(2-Me) Me O O OH I-58 Ph(3-Me) Me O O OH I-59 Ph(4-Me) Me O O OH I-60 Ph(2-OMe) Me O O OH I-61 Ph(3-OMe) Me O O OH I-62 Ph(4-OMe) Me O O OH I-63 Ph(2-CF₃) Me O O OH I-64 Ph(3-CF₃) Me O O OH I-65 Ph(4-CF₃) Me O O OH I-66 Ph(2-NO₂) Me O O OH I-67 Ph(3-NO₂) Me O O OH I-68 Ph(4-NO₂) Me O O OH I-69 Ph(2-OCF₃) Me O O OH I-70 Ph(3-OCF₃) Me O O OH I-71 Ph(4-OCF₃) Me O O OH I-72 Ph(2-CN) Me O O OH I-73 Ph(3-CN) Me O O OH I-74 Ph(4-CN) Me O O OH I-75 Ph(3,4-F₂) Me O O OH I-76 Ph(3,5-F₂) Me O O OH I-77 Ph(2,3-F₂) Me O O OH I-78 Ph(2,4-F₂) Me O O OH I-79 Ph(2,5-F₂) Me O O OH I-80 Ph(2,6-F₂) Me O O OH I-81 Ph(3,4-Cl₂) Me O O OH I-82 Ph(3,5-Cl₂) Me O O OH I-83 Ph(2,3-Cl₂) Me O O OH I-84 Ph(2,4-Cl₂) Me O O OH I-85 Ph(2,5-Cl₂) Me O O OH

TABLE 3 Compound No. R¹ R² Y Z R⁴ I-86 Ph(2,6-Cl₂) Me O O OH I-87 Ph(3,4-Me₂) Me O O OH I-88 Ph(3,5-Me₂) Me O O OH I-89 Ph(2,3-Me₂) Me O O OH I-90 Ph(2,4-Me₂) Me O O OH I-91 Ph(2,5-Me₂) Me O O OH I-92 Ph(2,6-Me₂) Me O O OH I-93 Ph(3,4-OMe₂) Me O O OH I-94 Ph(3,5-OMe₂) Me O O OH I-95 Ph(2,3-OMe₂) Me O O OH I-96 Ph(2,4-OMe₂) Me O O OH I-97 Ph(2,5-OMe₂) Me O O OH I-98 Ph(2,6-OMe₂) Me O O OH I-99 Ph(3-F-4-OMe) Me O O OH I-100 Ph(3-F-5-OMe) Me O O OH I-101 Ph(2-F-3-OMe) Me O O OH I-102 Ph(2-F-4-OMe) Me O O OH I-103 Ph(2-F-5-OMe) Me O O OH I-104 Ph(2-F-6-OMe) Me O O OH I-105 Ph(3-F-4-Me) Me O O OH I-106 Ph(3-F-5-Me) Me O O OH I-107 Ph(2-F-3-Me) Me O O OH I-108 Ph(2-F-4-Me) Me O O OH I-109 Ph(2-F-5-Me) Me O O OH I-110 Ph(2-F-6-Me) Me O O OH I-111 Ph(3-OMe-4-F) Me O O OH I-112 Ph(2-OMe-3-F) Me O O OH I-113 Ph(2-OMe-4-F) Me O O OH I-114 Ph(2-OMe-5-F) Me O O OH I-115 Ph(3-Me-4-F) Me O O OH I-116 Ph(2-Me-3-F) Me O O OH I-117 Ph(2-Me-4-F) Me O O OH I-118 Ph(2-Me-5-F) Me O O OH I-119 Ph(3-Cl-4-OMe) Me O O OH I-120 Ph(3-Cl-5-OMe) Me O O OH I-121 Ph(2-Cl-3-OMe) Me O O OH I-122 Ph(2-Cl-4-OMe) Me O O OH I-123 Ph(2-Cl-5-OMe) Me O O OH I-124 Ph(2-Cl-6-OMe) Me O O OH I-125 Ph(3-Cl-4-Me) Me O O OH I-126 Ph(3-Cl-5-Me) Me O O OH I-127 Ph(2-Cl-3-Me) Me O O OH I-128 Ph(2-Cl-4-Me) Me O O OH I-129 Ph(2-Cl-5-Me) Me O O OH

TABLE 4 Compound No. R¹ R² Y Z R⁴ I-130 Ph(2-Cl-6-Me) Me O O OH I-131 Ph(3-OMe-4-Cl) Me O O OH I-132 Ph(2-OMe-3-Cl) Me O O OH I-133 Ph(2-OMe-4-Cl) Me O O OH I-134 Ph(2-OMe-5-Cl) Me O O OH I-135 Ph(3-Me-4-Cl) Me O O OH I-136 Ph(2-Me-3-Cl) Me O O OH I-137 Ph(2-Me-4-Cl) Me O O OH I-138 Ph(2-Me-5-Cl) Me O O OH I-139 Ph(3-F-4-Cl) Me O O OH I-140 Ph(3-F-5-Cl) Me O O OH I-141 Ph(2-F-3-Cl) Me O O OH I-142 Ph(2-F-4-Cl) Me O O OH I-143 Ph(2-F-5-Cl) Me O O OH I-144 Ph(2-F-6-Cl) Me O O OH I-145 Ph(3-Cl-4-F) Me O O OH I-146 Ph(2-Cl-3-F) Me O O OH I-147 Ph(2-Cl-4-F) Me O O OH I-148 Ph(2-Cl-5-F) Me O O OH I-149 Ph(3-Me-4-OMe) Me O O OH I-150 Ph(3-Me-5-OMe) Me O O OH I-151 Ph(2-Me-3-OMe) Me O O OH I-152 Ph(2-Me-4-OMe) Me O O OH I-153 Ph(2-Me-5-OMe) Me O O OH I-154 Ph(2-Me-6-OMe) Me O O OH I-155 Ph(3-OMe-4-Me) Me O O OH I-156 Ph(2-OMe-3-Me) Me O O OH I-157 Ph(2-OMe-4-Me) Me O O OH I-158 Ph(2-OMe-5-Me) Me O O OH I-159 Ph(3-CN-4-OMe) Me O O OH I-160 Ph(3-OMe-4-CN) Me O O OH I-161 Ph(3-Me-4-CN) Me O O OH I-162 Ph(3-CN-4-Me) Me O O OH I-163 Ph(3-NO₂-4-OMe) Me O O OH I-164 Ph(3-OMe-4-NO₂) Me O O OH I-165 Ph(3-Me-4-NO₂) Me O O OH I-166 Ph(3-NO₂-4-Me) Me O O OH I-167 Ph(3,5-F₂-4-OMe) Me O O OH I-168 Ph(3,5-F₂-4-Me) Me O O OH I-169 Ph(3,4,5-(OMe)₃) Me O O OH

TABLE 5 Compound No. R¹ R² Y Z R⁴ I-170

Me O O OH I-171

Me O O OH I-172

Me O O OH I-173

Me O O OH I-174

Me O O OH I-175

Me O O OH I-176

Me O O OH I-177

Me O O OH I-178

Me O O OH I-179

Me O O OH I-180

Me O O OH I-181

Me O O OH I-182

Me O O OH I-183

Me O O OH I-184

Me O O OH

TABLE 6 Compound No. R¹ R² Y Z R⁴ I-185

Me O O OH I-186

Me O O OH I-187

Me O O OH I-188

Me O O OH I-189

Me O O OH I-190

Me O O OH I-191

Me O O OH I-192

Me O O OH I-193

Me O O OH I-194

Me O O OH I-195

Me O O OH I-196

Me O O OH I-197

Me O O OH I-198

Me O O OH I-199

Me O O OH I-200

Me O O OH

TABLE 7 Compound No. R¹ R² Y Z R⁴ I-201

Me O O OH I-202

Me O O OH I-203

Me O O OH I-204

Me O O OH I-205 CH₂Ph Me O O OH I-206 CH₂CH₂Ph Me O O OH I-207 CH₂CH₂CH₂Ph Me O O OH I-208 CH₂CH═CHPh Me O O OH I-209 CH₂C≡CPh Me O O OH I-210 CH₂CH═NOMe Me O O OH I-211 CH₂CH═NOEt Me O O OH I-212 CH₂CH═NOPr-n Me O O OH I-213 CH₂CH═NOPh Me O O OH I-214 CH₂CH(OMe)₂ Me O O OH I-215 CH₂CHO Me O O OH I-216 NH₂ Me O O OH I-217 NHMe Me O O OH I-218 NHEt Me O O OH I-219 NHPr-n Me O O OH I-220 NHPr-i Me O O OH I-221 NHBu-n Me O O OH I-222 NHBu-i Me O O OH I-223 NHBu-s Me O O OH I-224 NHCH₂Pr-c Me O O OH I-225 NHPen-n Me O O OH I-226 NHHex-n Me O O OH I-227 NHCH₂CH₂CH₂Cl Me O O OH I-228 NHCH₂CH₂CH₂F Me O O OH I-229 NHCH₂CH₂OMe Me O O OH I-230 NMe₂ Me O O OH I-231 NEt₂ Me O O OH I-232 N(Pr-n)₂ Me O O OH I-233 N(Bu-n)₂ Me O O OH I-234 N(Me)Et Me O O OH I-235 N(Me)CH₂CH₂OMe Me O O OH I-236 NHPh Me O O OH I-237 NHCH₂Ph Me O O OH I-238 N═OMe₂ Me O O OH I-239 N═OEt₂ Me O O OH

TABLE 8 Compound No. R¹ R² Y Z R⁴ I-240 N═CHNMe₂ Me O O OH I-241 NHC(═O)Me Me O O OH I-242 N[C(═O)Me]₂ Me O O OH I-243 NHC(═O)OMe Me O O OH I-244 N[C(═O)OMe]₂ Me O O OH I-245 NHSO₂Me Me O O OH I-246 NHSO₂Ph Me O O OH I-247 NHSO₂CH₂Ph Me O O OH I-248 OMe Me O O OH I-249 OEt Me O O OH I-250 OPr-n Me O O OH I-251 OPr-i Me O O OH I-252 OCH₂Pr-c Me O O OH I-253 OCH₂Cl Me O O OH I-254 OCHCl₂ Me O O OH I-255 OCCl₂ Me O O OH I-256 OCH₂F Me O O OH I-257 OCHF₂ Me O O OH I-258 OCF₂ Me O O OH I-259 Ph Et O O OH I-260 Ph Pr-i O O OH I-261 Ph CHF₂ O O OH I-262 Ph Ph O O OH I-263 Ph Me O O OH I-264 Ph Me O O OH I-265 Me Me O O OH I-266 Me Me O O OH I-267 Ph Me O O SPh I-268 Ph(4-OEt) Me O O OH I-269 Ph(2-Ph) Me O O OH I-270 Ph(3-Ph) Me O O OH I-271 Ph(4-Ph) Me O O OH I-272

Me O O OH I-273

Me O O OH I-274 Me

O O OH I-275 Et

O O OH I-276

Me O O OH

TABLE 9 Compnund No. R¹ R² Y Z R⁴ I-277

Me O O OH I-278

Me O O OH I-279

Me O O OH I-280

Me O O OH I-281

Me O O OH I-282 Ph(2-Me-4-Br) Me O O OH I-283 Ph(2-Me-4-I) Me O O OH I-284 Ph(2-Me-5-CF₃) Me O O OH I-285 Ph(2-Me-6-OCF₃) Me O O OH I-286 Ph(2-Pr-i) Me O O OH I-287

Me O O OH I-288 Ph(2-Et) Me O O OH I-289

Me O O OH I-290

Me O O OH I-291

Me O S OH I-292

Me O O OH I-293

Me O O OH I-294 CH₂COOBu-t Me O O OH I-295 (C₇H₁₄)CH₃ Me O O OH I-296 (C₉H₁₈)CH₃ Me O O OH I-297 Ph(2-F,4-Cl,5-OMe) Me O O OH I-298 Ph(2,3,4-(OMe)₃ Me O O OH I-299 Ph(3,5-Cl₂-4-OMe) Me O O OH I-300 Ph(3,5-Cl₂-4-SMe) Me O O OH I-301 Ph(3,5-Cl₂-4-SO₂Me) Me O O OH I-302 Ph(3,4,5-F₃) Me O O OH I-303

Me O O OH

TABLE 10 Compound No. R¹ R² Y Z R⁴ I-304

Me O O OH I-305

Me O O OH I-306 Bu-n

O O OH I-307 CH₂CH(CH₃)₂

O O OH I-308 Ph Pen-n O O OH I-309 H Me O O OH I-310 CH₂C≡CF Me O O OH I-311

Me O O OH I-312

Me O O OH I-313 CH₂NH₂ Me O O OH I-314 CH₂NO₂ Me O O OH I-315 CH₂NHCH₃ Me O O OH I-316 CH₂N(CH₃)₂ Me O O OH I-317 CH₂SCH₂CF₃ Me O O OH I-318 CH₂SOCH₂CF₃ Me O O OH I-319 CH₂SO₂CH₂CF₃ Me O O OH I-320 CH₂OH Me O O OH I-321 CH₂OBn Me O O OH I-322 CH₂OCH₂Pr-c Me O O OH I-323 CH₂OPh Me O O OH I-324 CH₂SPh Me O O OH I-325 CH₂SOPh Me O O OH I-326 CH₂SO₂Ph Me O O OH I-327 CH₂CON(CH₃)₂ Me O O OH I-328 CH₂COCH₃ Me O O OH I-329 CH₂OCOCH₃ Me O O OH I-330 CH₂ON═CHCH₃ Me O O OH I-331 C₂H₄OC₂H₄SCH₃ Me O O OH I-332 C₂H₄OC₂H₄SOCH₃ Me O O OH I-333 C₂H₄OC₂H₄SO₂CH₃ Me O O OH I-334 CH₂OCH₂CN Me O O OH I-335 CH₂CN Me O O OH I-336 OCH₂CH═CH₂ Me O O OH I-337 OCH₂C≡CH Me O O OH I-338 OPr-c Me O O OH

TABLE 11 Compound No. R¹ R² Y Z R⁴ I-339

Me O O OH I-340

Me O O OH I-341

Me O O OH I-342

Me O O OH I-343

Me O O OH I-344 Ph H O O OH I-345 Ph CH₂CH═CH₂ O O OH I-346 Ph CH₂C≡CH O O OH I-347 Ph Pr-c O O OH I-348 Ph CH₂CH═CF₂ O O OH I-349 Ph CH₂C≡CF O O OH I-350 Ph C₂H₄OCH₃ O O OH I-351 Ph C₂H₄OC₂H₅ O O OH I-352 Ph CH(Me)OEt O O OH I-353 Ph CH₂OPr-c O O OH I-354 Ph CH(OCH₃)₂ O O OH I-355 Ph CH₂Ph O O OH I-356 Ph

O O OH I-357 Ph

O O OH I-358 Ph Me O O NH₂ I-359 Ph Me O O Cl I-360 Ph Me O O CN I-361 Ph Me O O NCS I-362 Ph Me O O NCO I-363 Ph Me O O OCO₂H I-364 Ph Me O O OCO₂CH₃ I-365 Ph Me O O OCO₂CH₂Ph I-366 Ph Me O O OMe I-367 Ph Me O O OEt I-368 Ph Me O O OPr I-369 Ph Me O O OCH₂CH═CH₃ I-370 Ph Me O O OCH₂C≡OH I-371 Ph Me O O OPr-c I-372 Ph Me O O OBu-c I-373 Ph Me O O OPen-c

TABLE 12 Compound No. R¹ R² Y Z R⁴ I-374 Ph Me O O OHex-c I-375 Ph Me O O OCH₂CN I-376 Ph Me O O OCH₂Pr-c I-377 Ph Me O O OCOCH₃ I-378 Ph Me O O OCOCCl₃ I-379 Ph Me O O OCOCH═CH₂ I-380 Ph Me O O OCOCH═CF₂ I-381 Ph Me O O OCOCH₂C≡CH I-382 Ph Me O O OCOCH₂C≡CF I-383 Ph Me O O OCH₂CO₂CH₃ I-384 Ph Me O O OPh I-385 Ph Me O O OCH₂Ph I-386 Ph Me O O OCOPh I-387 Ph Me O O OCOCH₂Ph I-388 Ph Me O O OCH₂COPh I-389 Ph Me O O OSO₂CH₂CF₃ I-390 Ph Me O O OSO₂CH₂Ph I-391 Ph Me O O SCH₃ I-392 Ph Me O O SOCH₃ I-393 Ph Me O O SO₂CH₃ I-394 Ph Me O O SCH₂CF₃ I-395 Ph Me O O SOCH₂CF₃ I-396 Ph Me O O SO₂CH₂CF₃ I-397 Ph Me O O SCH₂CH═CH₂ I-398 Ph Me O O SOCH₂CH═CH₂ I-399 Ph Me O O SO₂CH₂CH═CH₂ I-400 Ph Me O O SCH₂CH≡CH I-401 Ph Me O O SOCH₂CH≡CH I-402 Ph Me O O SO₂CH₂CH≡CH I-403 Ph Me O O SCH₂Ph I-404 Ph Me O O SOPh I-405 Ph Me O O SOCH₂Ph I-406 Ph Me O O SO₂Ph I-407 Ph Me O O SO₂CH₂Ph I-408 Ph Me O O NHCH₃ I-409 Ph Me O O N(CH₃)₂ I-410 Ph Me O O NHCOCH₃ I-411 Ph Me O O

I-412 Ph Me O O

TABLE 13 Compound No. R¹ R² Y Z R⁴ I-413 Ph Me O O

I-414 Ph Me O O

I-415 Ph Me O O

I-416 Ph Me O O

I-417 (4-Pr-c)Ph Me O O OH I-418 (4-CH₂Pr-c)Ph Me O O OH I-419 (4-CH₂═CHCH₂)Ph Me O O OH I-420 (4-CH≡CCH₂)Ph Me O O OH I-421 (4-CH₂CH═CF₂)Ph Me O O OH I-422 (4-CH₂CH≡CF)Ph Me O O OH I-423

Me O O OH I-424

Me O O OH I-425

Me O O OH I-426

Me O O OH I-427

Me O O OH I-428

Me O O OH I-429 (4-OCHF₂)Ph Me O O OH I-430 (4-SMe)Ph Me O O OH I-431 (4-SOMe)Ph Me O O OH I-432 (4-SO₂Me)Ph Me O O OH I-433 (4-SCF₃)Ph Me O O OH I-434 (4-SOCF₃)Ph Me O O OH I-435 (4-SO₂CF₃)Ph Me O O OH I-436

Me O O OH I-437

Me O O OH

TABLE 14 Compound No. R¹ R² Y Z R⁴ I-438

Me O O OH I-439

Me O O OH I-440

Me O O OH I-441

Me O O OH I-442

Me O O OH I-443

Me O O OH I-444

Me O O OH I-445

Me O O OH I-446

Me O O OH I-447

Me O O OH I-448

Me O O OH I-449

Me O O OH I-450

Me O O OH I-451

Me O O OH I-452

Me O O OH I-453

Me O O OH I-454

Me O O OH I-455

Me O O OH

TABLE 15 Com- pound No. R¹ R² Y Z R⁴ I-456

Me O O OH I-457

Me O O OH I-458

Me O O OH I-459

Me O O OH I-460

Me O O OH I-461

Me O O OH I-462

Me O O OH I-463

Me O O OH I-464

Me O S OH I-465 Ph(3,4,5-Cl) Me O O OH I-466 N(Me)Ph Me O O OH I-467

Me O O OH I-468 CH₂CO(Bu-t) Me O O OH I-469 Ph(2,3,5,6-F₄) Me O O OH I-470 Ph[(3,5-(CF₃)₂] Me O O OH I-471 CH₂C(Me)═NOMe Me O O OH I-472 Ph(2,4,6-Me₃) Me O O OH I-473 Ph(2,3,4,5,6-F₅) Me O O OH I-474 N(Et)Ph Me O O OH I-475 N(Pr-i)Ph Me O O OH I-476 N(Me)Ph(4-F) Me O O OH I-477 Ph CH₂CF₃ O O OH I-478 CH₂C(Me)═NOEt Me O O OH I-479 CH₂C(Me)═NO(Pr-i) Me O O OH I-480 Ph(4-F) Me O S OH

TABLE 16

Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-1 Me Me O O Me H OH II-2 Et Me O O Me Me OH II-3 Pr-n Me O O Me H OH II-4 Pr-i Me O O Me H OH II-5 Bu-n Me O O Me H OH II-6 Bu-i Me O O Me H OH II-7 Bu-s Me O O Me Me OH II-8 Bu-t Me O O Me H OSO₂Pr II-9 Hex-n Me O O Me H OH II-10 CH₂CF₃ Me O O Me H OH II-11 CH₂CH═CH₂ Me O O Et H OH II-12 CH₂C(Me)═CH₂ Me O O Me H OH II-13 CH2CH₂CH═CMe₂ Me O O Me H OH II-14 CH₂C≡CH Me O O Me Me OH II-15 CH₂C≡CCH₃ Me O O Me H OSO₂Ph II-16 Pr-c Me O O Me H OH II-17 Bu-c Me O O i-Pr H OH II-18 Pen-c Me O O Me H OH II-19 Hex-c Me O O Et H OH II-20 CH₂Pr-c Me O O Me H OH II-21 CH₂Bu-c Me O O Me H OH II-22 CH₂Pen-c Me O O Me Me OH II-23 CH₂Hex-c Me O O Me H OH II-24 CH₂CH═CCl₂ Me O O Me H OSO₂Pr II-25 CH₂CCl═CHCl Me O O Me H OH II-26 CH₂CH₂CH═CCl₂ Me O O Et H OH II-27 CH₂CH₂C(Me)═CF₂ Me O O Me H OH II-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O Me H OH II-29 CH₂CH═CF₂ Me O O Me Me OH II-30 CH₂CH₂OMe Me O O Me H OH II-31 CH₂CH₂OEt Me O O Me H OH II-32 CH(Me)CH₂OMe Me O O Pr-i H OH II-33 CH₂CH₂OCH₂CH₂OMe Me O O Me H OH II-34 CH₂CH₂OPr-n Me O O Et H OH II-35 CH₂CH₂OPr-i Me O O Me H OH II-36 CH₂CH₂OPr-c Me O O Me Me OH II-37 CH₂CH₂OBu-c Me O O Me H OH II-38 CH₂CH₂OPen-c Me O O Me H OH II-39 CH₂CH₂OHex-c Me O O Me H OH

TABLE 17 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-40 CH₂CH₂OCH₂CF₃ Me O O Et Me OH II-41 CH₂CH₂CH₂OMe Me O O Me H OH II-42 CH═CHMe Me O O Me H OSO₂Ph II-43 CH₂SMe Me O O Me H OH II-44 CH₂SPr-n Me O O Me H OH II-45 CH₂CH₂SMe Me O O Pr-i H OH II-46 CH₂CH₂SOMe Me O O Me H OH II-47 CH₂CH₂SO₂Me Me O O Me Me OH II-48 CH₂CH₂CH₂SMe Me O O Et H OH II-49 CH₂CH₂CH₂SO₂Me Me O O Me H OH II-50 Ph Me O O Me H OH II-51 Ph(2-Cl) Me O O Me H OH II-52 Ph(3-Cl) Me O O Me H OH II-53 Ph(4-Cl) Me O O Me H OSO₂Pr II-54 Ph(2-F) Me O O Pr-i H OH II-55 Ph(3-F) Me O O Me H OH II-56 Ph(4-F) Me O O Me H OH II-57 Ph(2-Me) Me O O Me Me OH II-58 Ph(3-Me) Me O O Me H OH II-59 Ph(4-Me) Me O O Et H OH II-60 Ph(2-OMe) Me O O Me H OH II-61 Ph(3-OMe) Me O O Me H OH II-62 Ph(4-OMe) Me O O Me H OH II-63 Ph(2-CF₃) Me O O Me H OH II-64 Ph(3-CF₃) Me O O Pr-i H OSO₂Ph II-65 Ph(4-CF₃) Me O O Me H OH II-66 Ph(2-NO₂) Me O O Me H OH II-67 Ph(3-NO₂) Me O O Me H OH II-68 Ph(4-NO₂) Me O O Me Me OH II-69 Ph(2-OCF₃) Me O O Me H OH II-70 Ph(3-OCF₃) Me O O Et H OH II-71 Ph(4-OCF₃) Me O O Me H OH II-72 Ph(2-CN) Me O O Me H OH II-73 Ph(3-CN) Me O O Me H OH II-74 Ph(4-CN) Me O O Me H OH II-75 Ph(3,4-F₂) Me O O Pr-i H OH II-76 Ph(3,5-F₂) Me O O Me H OH II-77 Ph(2,3-F₂) Me O O Me Me OSO₂Pr II-78 Ph(2,4-F₂) Me O O Me H OH II-79 Ph(2,5-F₂) Me O O Me H OH

TABLE 18 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-80 Ph(2,6-F₂) Me O O Et Me OH II-81 Ph(3,4-Cl₂) Me O O Me H OH II-82 Ph(3,5-Cl₂) Me O O Me H OH II-83 Ph(2,3-Cl₂) Me O O Me H OH II-84 Ph(2,4-Cl₂) Me O O Me H OH II-85 Ph(2,5-Cl₂) Me O O Pr-i H OH II-86 Ph(2,6-Cl₂) Me O O Me H OH II-87 Ph(3,4-Me₂) Me O O Me H OH II-88 Ph(3,5-Me₂) Me O O Me H OH II-89 Ph(2,3-Me₂) Me O O Me Me OH II-90 Ph(2,4-Me₂) Me O O Me H OH II-91 Ph(2,5-Me₂) Me O O Me H OH II-92 Ph(2,6-Me₂) Me O O Me H OH II-93 Ph(3,4-(OMe)₂) Me O O Me H OH II-94 Ph(3,5-(OMe)₂) Me O O Me H OH II-95 Ph(2,3-(OMe)₂) Me O O Me H OH II-96 Ph(2,4-(OMe)₂) Me O O Pr-i H OH II-97 Ph(2,5-(OMe)₂) Me O O Me H OSO₂Ph II-98 Ph(2,6-(OMe)₂) Me O O Me H OH II-99 Ph(3-F-4-OMe) Me O O Me Me OH II-100 Ph(3-F-5-OMe) Me O O Me H OH II-101 Ph(2-F-3-OMe) Me O O Me H OH II-102 Ph(2-F-4-OMe) Me O O Me H OH II-103 Ph(2-F-5-OMe) Me O O Me H OH II-104 Ph(2-F-6-OMe) Me O O Me H OH II-105 Ph(3-F-4-Me) Me O O Me H OSO₂Pr II-106 Ph(3-F-5-Me) Me O O Me H OH II-107 Ph(2-F-3-Me) Me O O Me H OH II-108 Ph(2-F-4-Me) Me O O Me H OH II-109 Ph(2-F-5-Me) Me O O Me Me OH II-110 Ph(2-F-6-Me) Me O O Me H OH II-111 Ph(3-OMe-4-F) Me O O Me H OH II-112 Ph(2-OMe-3-F) Me O O Pr-i H OSO₂Ph(4-Me) II-113 Ph(2-OMe-4-F) Me O O Me H OH II-114 Ph(2-OMe-5-F) Me O O Me H OH II-115 Ph(3-Me-4-F) Me O O Me H OH II-116 Ph(2-Me-3-F) Me O O Me H OH II-117 Ph(2-Me-4-F) Me O O Me H OH II-118 Ph(2-Me-5-F) Me O O Me H OH II-119 Ph(3-Cl-4-OMe) Me O O Me Me OH II-120 Ph(3-Cl-5-OMe) Me O O Me H OH

TABLE 19 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-121 Ph(2-Cl-3-OMe) Me O O Me H OH II-122 Ph(2-Cl-4-OMe) Me O O Me H OSO₂Ph(4-Me) II-123 Ph(2-Cl-5-OMe) Me O O Pr-i H OH II-124 Ph(2-Cl-6-OMe) Me O O Me H OH II-125 Ph(3-Cl-4-Me) Me O O Me H OH II-126 Ph(3-Cl-5-Me) Me O O Me Me OH II-127 Ph(2-Cl-3-Me) Me O O Me H OH II-128 Ph(2-Cl-4-Me) Me O O Me H OH II-129 Ph(2-Cl-5-Me) Me O O Me H OH II-130 Ph(2-Cl-6-Me) Me O O Me H OH II-131 Ph(3-OMe-4-Cl) Me O O Me H OH II-132 Ph(2-OMe-3-Cl) Me O O Me H OSO₂Ph II-133 Ph(2-OMe-4-Cl) Me O O Pr-i H OH II-134 Ph(2-OMe-5-Cl) Me O O Me H OH II-135 Ph(3-Me-4-Cl) Me O O Me Me OH II-136 Ph(2-Me-3-Cl) Me O O Me H OH II-137 Ph(2-Me-4-Cl) Me O O Me H OH II-138 Ph(2-Me-5-Cl) Me O O Me H OH II-139 Ph(3-F-4-Cl) Me O O Me H OSO₂Ph(4-Me) II-140 Ph(3-F-5-Cl) Me O O Me H OH II-141 Ph(2-F-3-Cl) Me O O Me H OH II-142 Ph(2-F-4-Cl) Me O O Me H OH II-143 Ph(2-F-5-Cl) Me O O Me H OH II-144 Ph(2-F-6-Cl) Me O O Me H OH II-145 Ph(3-Cl-4-F) Me O O Me H OH II-146 Ph(2-Cl-3-F) Me O O Me Me OH II-147 Ph(2-Cl-4-F) Me O O Me H OH II-148 Ph(2-Cl-5-F) Me O O Pr-i H OH II-149 Ph(3-Me-4-OMe) Me O O Me H OH II-150 Ph(3-Me-5-OMe) Me O O Me H OH II-151 Ph(2-Me-3-OMe) Me O O Me H OSO₂Ph(4-Me) II-152 Ph(2-Me-4-OMe) Me O O Me H OH II-153 Ph(2-Me-5-OMe) Me O O Me H OH II-154 Ph(2-Me-6-OMe) Me O O Me H OH II-155 Ph(3-OMe-4-Me) Me O O Me Me OH II-156 Ph(2-OMe-3-Me) Me O O Me H OH II-157 Ph(2-OMe-4-Me) Me O O Me H OH II-158 Ph(2-OMe-5-Me) Me O O Me Me OH II-159 Ph(3-CN-4-OMe) Me O O Me H OH II-160 Ph(3-OMe-4-CN) Me O O Me H OH II-161 Ph(3-Me-4-CN) Me O O Pr-i H OSO₂Ph(4-Me)

TABLE 20 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-162 Ph(3-CN-4-Me) Me O O Me H OH II-163 Ph(3-NO₂-4-OMe) Me O O Me H OH II-164 Ph(3-OMe-4-NO₂) Me O O Me H OH II-165 Ph(3-Me-4-NO₂) Me O O Me H OH II-166 Ph(3-NO₂-4-Me) Me O O Me H OH II-167 Ph(3,5-F₂-5-OMe) Me O O Me H OH II-168 Ph(3,5-F₂-5-Me) Me O O Me Me OH II-169 Ph(3,4,5-(OMe)₃) Me O O Me H OH II-170

Me O O Me H OH II-171

Me O O Me H OH II-172

Me O O Pr-i H OSO₂Ph(4-Me) II-173

Me O O Me H OH II-174

Me O O Me H OH II-175

Me O O Me Me OH II-176

Me O O Me H OH II-177

Me O O Me H OH II-178

Me O O Me H OH II-179

Me O O Me H OH II-180

Me O O Me H OH

TABLE 21 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-181

Me O O Me H OH II-182

Me O O Me H OH II-183

Me O O Me H OH II-184

Me O O Pr-i H Me II-185

Me O O Me Me OH II-186

Me O O Me H OH II-187

Me O O Me H OH II-188

Me O O Me H OH II-189

Me O O Me H OSO₂Ph(4-Me) II-190

Me O O Me H OH II-191

Me O O Me H OH II-192

Me O O Me H OH II-193

Me O O Me H OH II-194

Me O O Me H OH

TABLE 22 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-195

Me O O Me H OH II-196

Me O O Me H OH II-197

Me O O Me H OH II-198

Me O O Me H OH II-199

Me O O Pr-i Me OH II-200

Me O O Me H OH II-201

Me O O Me H OH II-202

Me O O Me H OH II-203

Me O O Me H OH II-204

Me O O Me Me OH II-205 CH₂Ph Me O O Me H OH II-206 CH₂CH₂Ph Me O O Me H OH II-207 CH₂CH₂CH₂Ph Me O O Me H OH II-208 CH₂CH═CHPh Me O O Me H OH II-209 CH₂C≡CPh Me O O Me H OH II-210 CH₂CH═NOMe Me O O Me H OH II-211 CH₂CH═NHEt Me O O Me H OH II-212 CH₂CH═NOPr-n Me O O Me H OH II-213 CH₂CH═NOPh Me O O Me Me OH II-214 CH₂CH(OMe)₂ Me O O Me H OH II-215 CH₂CHO Me O O Et H OH II-216 NH₂ Me O O Me H OH II-217 NHMe Me O O Me H OH II-218 NHEt Me O O Me H OH

TABLE 23 Com- pound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-219 NHPr-n Me O O Me H OSO₂Ph(4-Me) II-220 NHPr-i Me O O Me H OH II-221 NHBu-n Me O O Pr-i H OH II-222 NHBu-i Me O O Me H OH II-223 NHBu-s Me O O Me Me OH II-224 NHCH₂Pr-c Me O O Me H OH II-225 NHPen-n Me O O Me H OH II-226 NHHex-n Me O O Me H OH II-227 NHCH₂CH₂CH₂Cl Me O O Me H OH II-228 NHCH₂CH₂CH₂F Me O O Me H OH II-229 NHCH₂CH₂OMe Me O O Me H OH II-230 NMe₂ Me O O Me H OH II-231 NEt₂ Me O O Me H OH II-232 N(Pr-n)₂ Me O O Me H OH II-233 N(Bu-n)₂ Me O O Me H OH II-234 N(Me)Et Me O O Me Me OH II-235 N(Me)CH₂CH₂OMe Me O O Et H OH II-236 NHPh Me O O Me H OH II-237 NHCH₂Ph Me O O Me H OH II-238 N═CMe₂ Me O O Me H OH II-239 N═CEt₂ Me O O Me H OSO₂Ph(4-Me) II-240 N═CHNMe₂ Me O O Me H OH II-241 NHC(═O)Me Me O O Me H OH II-242 N[C(═O)Me]₂ Me O O Me H OH II-243 NHC(═O)OMe Me O O Pr-i H OH II-244 N[C(═O)OMe]₂ Me O O Me H OH II-245 NHSO₂Me Me O O Me H OH II-246 NHSO₂Ph Me O O Me Me OH II-247 NHSO₂CH₂Ph Me O O Me H OH II-248 OMe Me O O Et H OH II-249 OEt Me O O Me H OH II-250 OPr-n Me O O Me H OH II-251 OPr-i Me O O Me H OH II-252 OCH₂Pr-c Me O O Me H OH II-253 OCH₂Cl Me O O Me H OH II-254 OCHCl₂ Me O O Me H OH II-255 OCCl₃ Me O O Me Me OH II-256 OCH₂F Me O O Me H OH II-257 OCHF₂ Me O O Me H OH II-258 OCF₃ Me O O Me H OSO₂Ph(4-Me) II-259 Ph Et O O Et H OH II-260 Ph Pr-i O O Me H OH II-261 Ph CHF2 O O Me H OH

TABLE 24 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-262 Ph Ph O O Me H OH II-263 Ph Me O S Me Me OH II-264 Ph Me S S Me H OH II-265 Me Me O S Me H OH II-266 Me Me S S Me H OH II-267 Ph Me O O Pr-i H OSO₂Pr II-268 Ph(4-OEt) Me O O Me H OH II-269 Ph(2-Ph) Me O O Me H OH II-270 Ph(3-Ph) Me O O Me H OH II-271 Ph(4-Ph) Me O O Me H OH II-272

Me O O Me Me OH II-273

Me O O Et H OSO₂Ph(4-Me) II-274 Me

O O Me H OH II-275 Et

O O Me H OH II-276 H Me O O Me H OH II-277 CH₂C≡CF Me O O Me H OH II-278

Me O O Me H OH II-279

Me O O Me H OH II-280 CH₂NH₂ Me O O Me H OH II-281 CH₂NO₂ Me O O Me H OH II-282 CH₂NHCH₃ Me O O Me H OH II-283 CH₂N(CH₃)₂ Me O O Me H OH II-284 CH₂SCH₂CF₃ Me O O Me H OH II-285 CH₂SOCH₂CF₃ Me O O Me H OH II-286 CH₂SO₂CH₂CF₃ Me O O Me H OH II-287 CH₂OH Me O O Me H OH II-288 CH₂OBn Me O O Me H OH II-289 CH₂OCH₂Pr-c Me O O Me H OH

TABLE 25 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-290 CH₂OPh Me O O Me H OH II-291 CH₂SPh Me O O Me H OH II-292 CH₂SOPh Me O O Me H OH II-293 CH₂SO₂Ph Me O O Me H OH II-294 CH₂CON(CH₃)₂ Me O O Me H OH II-295 CH₂COCH₃ Me O O Me H OH II-296 CH₂OCOCH₃ Me O O Me H OH II-297 CH₂ON═CHCH₃ Me O O Me H OH II-298 C₂H₄OC₂H₄SCH₃ Me O O Me H OH II-299 C₂H₄OC₂H₄SOCH₃ Me O O Me H OH II-300 C₂H₄OC₂H₄SO₂CH₃ Me O O Me H OH II-301 CH₂OCH₂CN Me O O Me H OH II-302 CH₂CN Me O O Me H OH II-303 OCH₂CH═CH₂ Me O O Me H OH II-304 OCH₂C≡CH Me O O Me H OH II-305 OPr-c Me O O Me H OH II-306

Me O O Me H OH II-307

Me O O Me H OH II-308

Me O O Me H OH II-309

Me O O Me H OH II-310

Me O O Me H OH II-311 Ph H O O Me H OH II-312 Ph CH₂CH═CH₂ O O Me H OH II-313 Ph OCH₂C≡CH O O Me H OH II-314 Ph Pr-c O O Me H OH II-315 Ph CH₂CH═CF₂ O O Me H OH II-316 Ph CH₂C≡CF O O Me H OH II-317 Ph C₂H₄OCH₃ O O Me H OH II-318 Ph C₂H₄OC₂H₅ O O Me H OH II-319 Ph CH(Me)OEt O O Me H OH II-320 Ph CH₂OPr-c O O Me H OH II-321 Ph CH(OCH₃)₂ O O Me H OH II-322 Ph CH₂Ph O O Me H OH

TABLE 26 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-323 Ph

O O Me H OH II-324 Ph

O O Me H OH II-325 Ph Me O O Me H NH₂ II-326 Ph Me O O Me H Cl II-327 Ph Me O O Me H CN II-328 Ph Me O O Me H NCS II-329 Ph Me O O Me H NCO II-330 Ph Me O O Me H OCO₂H II-331 Ph Me O O Me H OCO₂CH₃ II-332 Ph Me O O Me H OCO₂CH₂Ph II-333 Ph Me O O Me H OMe II-334 Ph Me O O Me H OEt II-335 Ph Me O O Me H OPr II-336 Ph Me O O Me H OCH₂CH═CH₂ II-337 Ph Me O O Me H OCH₂C≡CH II-338 Ph Me O O Me H OPr-c II-339 Ph Me O O Me H OBu-c II-340 Ph Me O O Me H OPen-c II-341 Ph Me O O Me H OHex-c II-342 Ph Me O O Me H OCH₂CN II-343 Ph Me O O Me H OCH₂Pr-c II-344 Ph Me O O Me H OCOCH₃ II-345 Ph Me O O Me H OCOCCl₂ II-346 Ph Me O O Me H OCOCH═CH₂ II-347 Ph Me O O Me H OCOCH═CF₂ II-348 Ph Me O O Me H OCOCH₂C≡CH II-349 Ph Me O O Me H OCOCH₂C≡CF II-350 Ph Mc O O Me H OCH₂CO₂CH₃ II-351 Ph Me O O Me H OPh II-352 Ph Me O O Me H OCH₂Ph II-353 Ph Me O O Me H OCOPh II-354 Ph Me O O Me H OCOCH₂Ph II-355 Ph Me O O Me H OCH₂COPh II-356 Ph Me O O Me H OSO₂CH₂CF₃ II-357 Ph Me O O Me H OSO₂CH₂Ph II-356 Ph Me O O Me H SCH₃ II-359 Ph Me O O Me H SOCH₃ II-360 Ph Me O O Me H SO₂CH₃ II-361 Ph Me O O Me H SCH₂CF₃ II-362 Ph Me O O Me H SOCH₂CF₂ II-363 Ph Me O O Me H SO₂CH₂CF₃

TABLE 27 Compound No. R¹ R² Y Z R²⁰ R²¹ R⁴ II-364 Ph Me O O Me H SCH₂CH═CH₂ II-365 Ph Me O O Me H SOCH₂CH═CH₂ II-366 Ph Me O O Me H SO₂CH₂CH═CH₂ II-367 Ph Me O O Me H SCH₂CH≡CH II-368 Ph Me O O Me H SOCH₂CH≡CH II-369 Ph Me O O Me H SO₂CH₂CH≡CH II-370 Ph Me O O Me H SCH₂Ph II-371 Ph Me O O Me H SOPh II-372 Ph Me O O Me H SOCH₂Ph II-373 Ph Me O O Me H SO₂Ph II-374 Ph Me O O Me H SO₂CH₂Ph II-375 Ph Me O O Me H NHCH₃ II-376 Ph Me O O Me H N(CH₃)₂ II-377 Ph Me O O Me H NHCOCH₃ II-378 Ph Me O O Me H

II-379 Ph Me O O Me H

II-380 Ph Me O O Me H

II-381 Ph Me O O Me H

II-382 Ph Me O O Me H

II-383 Ph Me O O Me H

TABLE 28

Compound No. R¹ R² Y Z R⁴ III-1  Me Me O O OH III-2  Et Me O O OH III-3  Pr-n Me O O OH III-4  Pr-i Me O O OH III-5  Bu-n Me O O OH III-6  Bu-i Me O O OH III-7  Bu-s Me O O OH III-8  Bu-t Me O O OH III-9  Hex-n Me O O OH III-10 CH₂CF₃ Me O O OH III-11 CH₂CH═CH₂ Me O O OH III-12 CH₂C(Me)═CH₂ Me O O OH III-13 CH₂CH₂CH═CMe₂ Me O O OH III-14 CH₂C≡CH Me O O OH III-15 CH₂C≡CCH₃ Me O O OH III-16 Pr-c Me O O OH III-17 Bu-c Me O O OH III-18 Pen-c Me O O OH III-19 Hex-c Me O O OH III-20 CH₂Pr-c Me O O OH III-21 CH₂Bu-c Me O O OH III-22 CH₂Pen-c Me O O OH III-23 CH₂Hex-c Me O O OH III-24 CH₂CH═CCl₂ Me O O OH III-25 CH₂CCl═CHCl Me O O OH III-26 CH₂CH₂CH═CCl₂ Me O O OH III-27 CH₂CH₂C(Me)═CF₂ Me O O OH III-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O OH III-29 CH₂CH═CF₂ Me O O OH III-30 CH₂CH₂OMe Me O O OH III-31 CH₂CH₂OEt Me O O OH III-32 CH(Me)CH₂OMe Me O O OH III-33 CH₂CH₂OCH₂CH₂OMe Me O O OH III-34 CH₂CH₂OPr-n Me O O OH III-35 CH₂CH₂OPr-i Me O O OH III-36 CH₂CH₂OPr-c Me O O OH III-37 CH₂CH₂OBu-c Me O O OH III-38 CH₂CH₂OPen-c Me O O OH

TABLE 29 Compound No. R¹ R² Y Z R⁴ III-39 CH₂CH₂OHex-c Me O O OH III-40 CH₂CH₂OCH₂CF₃ Me O O OH III-41 CH₂CH₂CH₂OMe Me O O OH III-42 CH═CHMe Me O O OH III-43 CH₂SMe Me O O OH III-44 CH₂SPr-n Me O O OH III-45 CH₂CH₂SMe Me O O OH III-46 CH₂CH₂SOMe Me O O OH III-47 CH₂CH₂SO₂Me Me O O OH III-48 CH₂CH₂CH₂SMe Me O O OH III-49 CH₂CH₂CH₂SO₂Me Me O O OH III-50 Ph Me O O OH III-51 Ph(2-Cl) Me O O OH III-52 Ph(3-Cl) Me O O OH III-53 Ph(4-Cl) Me O O OH III-54 Ph(2-F) Me O O OH III-55 Ph(3-F) Me O O OH III-56 Ph(4-F) Me O O OH III-57 Ph(2-Me) Me O O OH III-58 Ph(3-Me) Me O O OH III-59 Ph(4-Me) Me O O OH III-60 Ph(2-OMe) Me O O OH III-61 Ph(3-OMe) Me O O OH III-62 Ph(4-OMe) Me O O OH III-63 Ph(2-CF₃) Me O O OH III-64 Ph(3-CF₃) Me O O OH III-65 Ph(4-CF₃) Me O O OH III-66 Ph(2-NO₂) Me O O OH III-67 Ph(3-NO₂) Me O O OH III-68 Ph(4-NO₂) Me O O OH III-69 Ph(2-OCF₃) Me O O OH III-70 Ph(3-OCF₃) Me O O OH III-71 Ph(4-OCF₃) Me O O OH III-72 Ph(2-CN) Me O O OH III-73 Ph(3-CN) Me O O OH III-74 Ph(4-CN) Me O O OH III-75 Ph(3,4-F₂) Me O O OH III-76 Ph(3,5-F₂) Me O O OH III-77 Ph(2,3-F₂) Me O O OH III-78 Ph(2,4-F₂) Me O O OH

TABLE 30 Compound No. R¹ R² Y Z R⁴ III-79 Ph(2,5-F₂) Me O O OH III-80 Ph(2,6-F₂) Me O O OH III-81 Ph(3,4-Cl₂) Me O O OH III-82 Ph(3,5-Cl₂) Me O O OH III-83 Ph(2,3-Cl₂) Me O O OH III-84 Ph(2,4-Cl₂) Me O O OH III-85 Ph(2,5-Cl₂) Me O O OH III-86 Ph(2,6-Cl₂) Me O O OH III-87 Ph(3,4-Me₂) Me O O OH III-88 Ph(3,5-Me₂) Me O O OH III-89 Ph(2,3-Me₂) Me O O OH III-90 Ph(2,4-Me₂) Me O O OH III-91 Ph(2,5-Me₂) Me O O OH III-92 Ph(2,6-Me₂) Me O O OH III-93 Ph(3,4-(OMe)₂) Me O O OH III-94 Ph(3,5-(OMe)₂) Me O O OH III-95 Ph(2,3-(OMe)₂) Me O O OH III-96 Ph(2,4-(OMe)₂) Me O O OH III-97 Ph(2,5-(OMe)₂) Me O O OH III-98 Ph(2,6-(OMe)₂) Me O O OH III-99 Ph(3-F-4-OMe) Me O O OH III-100 Ph(3-F-5-OMe) Me O O OH III-101 Ph(2-F-3-OMe) Me O O OH III-102 Ph(2-F-4-OMe) Me O O OH III-103 Ph(2-F-5-OMe) Me O O OH III-104 Ph(2-F-6-OMe) Me O O OH III-105 Ph(3-F-4-Me) Me O O OH III-106 Ph(3-F-5-Me) Me O O OH III-107 Ph(2-F-3-Me) Me O O OH III-108 Ph(2-F-4-Me) Me O O OH III-109 Ph(2-F-5-Me) Me O O OH III-110 Ph(2-F-6-Me) Me O O OH III-111 Ph(3-OMe-4-F) Me O O OH III-112 Ph(2-OMe-3-F) Me O O OH III-113 Ph(2-OMe-4-F) Me O O OH III-114 Ph(2-OMe-5-F) Me O O OH III-115 Ph(3-Me-4-F) Me O O OH III-116 Ph(2-Me-3-F) Me O O OH III-117 Ph(2-Me-4-F) Me O O OH

TABLE 31 Compound No. R¹ R² Y Z R⁴ III-118 Ph(2-Me-5-F) Me O O OH III-119 Ph(3-Cl-4-OMe) Me O O OH III-120 Ph(3-Cl-5-OMe) Me O O OH III-121 Ph(2-Cl-3-OMe) Me O O OH III-122 Ph(2-Cl-4-OMe) Me O O OH III-123 Ph(2-Cl-5-OMe) Me O O OH III-124 Ph(2-Cl-6-OMe) Me O O OH III-125 Ph(3-Cl-4-Me) Me O O OH III-126 Ph(3-Cl-5-Me) Me O O OH III-127 Ph(2-Cl-3-Me) Me O O OH III-128 Ph(2-Cl-4-Me) Me O O OH III-129 Ph(2-Cl-5-Me) Me O O OH III-130 Ph(2-Cl-6-Me) Me O O OH III-131 Ph(3-OMe-4-Cl) Me O O OH III-132 Ph(2-OMe-3-Cl) Me O O OH III-133 Ph(2-OMe-4-Cl) Me O O OH III-134 Ph(2-OMe-5-Cl) Me O O OH III-135 Ph(3-Me-4-Cl) Me O O OH III-136 Ph(2-Me-3-Cl) Me O O OH III-137 Ph(2-Me-4-Cl) Me O O OH III-138 Ph(2-Me-5-Cl) Me O O OH III-139 Ph(3-F-4-Cl) Me O O OH III-140 Ph(3-F-5-Cl) Me O O OH III-141 Ph(2-F-3-Cl) Me O O OH III-142 Ph(2-F-4-Cl) Me O O OH III-143 Ph(2-F-5-Cl) Me O O OH III-144 Ph(2-F-6-Cl) Me O O OH III-145 Ph(3-Cl-4-F) Me O O OH III-146 Ph(2-Cl-3-F) Me O O OH III-147 Ph(2-Cl-4-F) Me O O OH III-148 Ph(2-Cl-5-F) Me O O OH III-149 Ph(3-Me-4-OMe) Me O O OH III-150 Ph(3-Me-5-OMe) Me O O OH III-151 Ph(2-Me-3-OMe) Me O O OH III-152 Ph(2-Me-4-OMe) Me O O OH III-153 Ph(2-Me-5-OMe) Me O O OH III-154 Ph(2-Me-6-OMe) Me O O OH III-155 Ph(3-OMe-4-Me) Me O O OH III-156 Ph(2-OMe-3-Me) Me O O OH

TABLE 32 Compound No. R¹ R² Y Z R⁴ III-157 Ph(2-OMe-4-Me) Me O O OH III-158 Ph(2-OMe-5-Me) Me O O OH III-159 Ph(3-CN-4-OMe) Me O O OH III-160 Ph(3-OMe-4-CN) Me O O OH III-161 Ph(3-Me-4-CN) Me O O OH III-162 Ph(3-CN-4-Me) Me O O OH III-163 Ph(3-NO₂-4-OMe) Me O O OH III-164 Ph(3-OMe-4-NO₂) Me O O OH III-165 Ph(3-Me-4-NO₂) Me O O OH III-166 Ph(3-NO₂-4-Me) Me O O OH III-167 Ph(3,5-F₂-5-OMe) Me O O OH III-168 Ph(3,5-F₂-5-Me) Me O O OH III-169 Ph(3,4,5-(OMe)₃) Me O O OH III-170

Me O O OH III-171

Me O O OH III-172

Me O O OH III-173

Me O O OH III-174

Me O O OH III-175

Me O O OH III-176

Me O O OH III-177

Me O O OH III-178

Me O O OH

TABLE 33 Compound No. R¹ R² Y Z R⁴ III-179

Me O O OH III-180

Me O O OH III-181

Me O O OH III-182

Me O O OH III-183

Me O O OH III-184

Me O O OH III-185

Me O O OH III-186

Me O O OH III-187

Me O O OH III-188

Me O O OH III-189

Me O O OH III-190

Me O O OH III-191

Me O O OH III-192

Me O O OH

TABLE 34 Compound No. R¹ R² Y Z R⁴ III-193

Me O O OH III-194

Me O O OH III-195

Me O O OH III-196

Me O O OH III-197

Me O O OH III-198

Me O O OH III-199

Me O O OH III-200

Me O O OH III-201

Me O O OH III-202

Me O O OH III-203

Me O O OH III-204

Me O O OH III-205 CH₂Ph Me O O OH III-206 CH₂CH₂Ph Me O O OH III-207 CH₂CH₂CH₂Ph Me O O OH III-208 CH₂CH═CHPh Me O O OH III-209 CH₂C≡CPh Me O O OH III-210 CH₂CH═NOMe Me O O OH III-211 CH₂CH═NOEt Me O O OH

TABLE 35 Compound No. R¹ R² Y Z R⁴ III-212 CH₂CH═NOPr-n Me O O OH III-213 CH₂CH═NOPh Me O O OH III-214 CH₂CH(OMe)₂ Me O O OH III-215 CH₂CHO Me O O OH III-216 NH₂ Me O O OH III-217 NHMe Me O O OH III-218 NHEt Me O O OH III-219 NHPr-n Me O O OH III-220 NHPr-i Me O O OH III-221 NHBu-n Me O O OH III-222 NHBu-i Me O O OH III-223 NHBu-s Me O O OH III-224 NHCH₂Pr-c Me O O OH III-225 NHPan-n Me O O OH III-226 NHHex-n Me O O OH III-227 NHCH₂CH₂CH₂Cl Me O O OH III-228 NHCH₂CH₂CH₂F Me O O OH III-229 NHCH₂CH₂OMe Me O O OH III-230 NMe₂ Me O O OH III-231 NEt₂ Me O O OH III-232 N(Pr-n)₂ Me O O OH III-233 N(Bu-n)₂ Me O O OH III-234 N(Me)Et Me O O OH III-235 N(Me)CH₂CH₂OMe Me O O OH III-236 NHPh Me O O OH III-237 NHCH₂Ph Me O O OH III-238 N═CMe₂ Me O O OH III-239 N═CEt₂ Me O O OH III-240 N═CHNMe₂ Me O O OH III-241 NHC(═O)Me Me O O OH III-242 N[C(═O)Me]₂ Me O O OH III-243 NHC(═O)OMe Me O O OH III-244 N[C(═O)OMe]₂ Me O O OH III-245 NHSO₂Me Me O O OH III-246 NHSO₂Ph Me O O OH III-247 NHSO₂CH₂Ph Me O O OH III-248 OMe Me O O OH III-249 OEt Me O O OH III-250 OPr-n Me O O OH III-251 OPr-i Me O O OH III-252 OCH₂Pr-c Me O O OH III-253 OCH₂Cl Me O O OH III-254 OCHCl₂ Me O O OH

TABLE 36 Compound No. R¹ R² Y Z R⁴ III-255 OCCl₃ Me O O OH III-256 OCH₂F Me O O OH III-257 OCHF₂ Me O O OH III-258 OCF₃ Me O O OH III-259 Ph Et O O OH III-260 Ph Pr-i O O OH III-261 Ph CHF₂ O O OH III-262 Ph Ph O O OH III-263 Ph Me O S OH III-264 Ph Me S S OH III-265 Me Me O S OH III-266 Me Me S S OH III-267 Ph Me O O SPh III-268 Ph(4-OEt) Me O O OH III-269 Ph(2-Ph) Me O O OH III-270 Ph(3-Ph) Me O O OH III-271 Ph(4-Ph) Me O O OH III-272

Me O O OH III-273

Me O O OH III-274 Me

O O OH III-275 Et

O O OH III-276 H Me O O OH III-277 CH₂C≡CF Me O O OH III-278

Me O O OH III-279

Me O O OH III-280 CH₂NH₂ Me O O OH III-281 CH₂NO₂ Me O O OH III-282 CH₂NHCH₃ Me O O OH III-283 CH₂N(CH₃)₂ Me O O OH III-284 CH₂SCH₂CF₃ Me O O OH III-285 CH₂SOCH₂CF₃ Me O O OH III-286 CH₂SO₂CH₂CF₃ Me O O OH III-287 CH₂OH Me O O OH III-288 CH₂OBn Me O O OH III-289 CH₂OCH₂Pr-c Me O O OH

TABLE 37 Compound No. R¹ R² Y Z R⁴ III-290 CH₂OPh Me O O OH III-291 CH₂SPh Me O O OH III-292 CH₂SOPh Me O O OH III-293 CH₂SO₂Ph Me O O OH III-294 CH₂CON(CH₃)₂ Me O O OH III-295 CH₂COCH₂ Me O O OH III-296 CH₂OCOCH₃ Me O O OH III-297 CH₂ON═CHCH₃ Me O O OH III-298 C₂H₄OC₂H₄SCH₃ Me O O OH III-299 C₂H₄OC₂H₄SOCH₃ Me O O OH III-300 C₂H₄OC₂H₄SO₂CH₃ Me O O OH III-301 CH₂OCH₂CN Me O O OH III-302 CH₂CN Me O O OH III-303 OCH₂CH═CH₂ Me O O OH III-304 OCH₂C≡CH Me O O OH III-305 OPr-c Me O O OH III-306

Me O O OH III-307

Me O O OH III-308

Me O O OH III-309

Me O O OH III-310

Me O O OH III-311 Ph H O O OH III-312 Ph CH₂CH═CH₂ O O OH III-313 Ph CH₂C≡CH O O OH III-314 Ph Pr-c O O OH III-315 Ph CH₂CH═CF₂ O O OH III-316 Ph CH₂C≡CF O O OH III-317 Ph C₂H₄OCH₃ O O OH III-318 Ph C₂H₄OC₂H₅ O O OH III-319 Ph CH(Me)OEt O O OH III-320 Ph CH₂OPr-c O O OH III-321 Ph CH(OCH₃)₂ O O OH III-322 Ph CH₂Ph O O OH III-323 Ph

O O OH

TABLE 38 Com- pound No. R¹ R² Y Z R⁴ III-324 Ph

O O OH III-325 Ph Me O O NH₂ III-326 Ph Me O O Cl III-327 Ph Me O O CN III-328 Ph Me O O NCS III-329 Ph Me O O NCO III-330 Ph Me O O OCO₂H III-331 Ph Me O O OCO₂CH₃ III-332 Ph Me O O OCO₂CH₂Ph III-333 Ph Me O O OMe III-334 Ph Me O O OEt III-335 Ph Me O O OPr III-336 Ph Me O O OCH₂CH═CH₂ III-337 Ph Me O O OCH₂C≡CH III-338 Ph Me O O OPr-c III-339 Ph Me O O OBu-c III-340 Ph Me O O OPen-c III-341 Ph Me O O OHex-c III-342 Ph Me O O OCH₂CN III-343 Ph Me O O OCH₂Pr-c III-344 Ph Me O O OCOCH₃ III-345 Ph Me O O OCOCCl₃ III-346 Ph Me O O OCOCH═CH₂ III-347 Ph Me O O OCOCH═CF₂ III-348 Ph Me O O OCOCH₂C≡CH III-349 Ph Me O O OCOCH₂C≡CF III-350 Ph Me O O OCH₂CO₂CH₃ III-351 Ph Me O O OPh III-352 Ph Me O O OCH₂Ph III-353 Ph Me O O OCOPh III-354 Ph Me O O OCOCH₂Ph III-355 Ph Me O O OCH₂COPh III-356 Ph Me O O OSO₂CH₂CF₃ III-357 Ph Me O O OSO₂CH₂Ph III-358 Ph Me O O SCH₃ III-359 Ph Me O O SOCH₃ III-360 Ph Me O O SO₂CH₃ III-361 Ph Me O O SCH₂CF₃ III-362 Ph Me O O SOCH₂CF₃ III-363 Ph Me O O SO₂CH₂CF₃ III-364 Ph Me O O SCH₂CH═CH₂ III-365 Ph Me O O SOCH₂CH═CH₂ III-366 Ph Me O O SO₂CH₂CH═CH₂

TABLE 39 Compound No. R¹ R² Y Z R⁴ III-367 Ph Me O O SCH₂CH≡CH III-368 Ph Me O O SOCH₂CH≡CH III-369 Ph Me O O SO₂CH₂CH≡CH III-370 Ph Me O O SCH₂Ph III-371 Ph Me O O SOPh III-372 Ph Me O O SOCH₂Ph III-373 Ph Me O O SO₂Ph III-374 Ph Me O O SO₂CH₂Ph III-375 Ph Me O O NHCH₃ III-376 Ph Me O O N(CH₃)₂ III-377 Ph Me O O NHCOCH₃ III-378 Ph Me O O

III-379 Ph Me O O

III-380 Ph Me O O

III-381 Ph Me O O

III-382 Ph Me O O

III-383 Ph Me O O

TABLE 40

Compound No. R¹ A₁ A₂ A₃ VI-1  Ph C(CH₃)₂ CO C(CH₃)₂ VI-2  Ph CHCH₃ CH₂ CH₂ VI-3  Ph CH₂ CHCH₃ CH₂ VI-4  Ph CHCH₃ CHCH₃ CHCH₃ VI-5  Ph C(CH₃)₂ CH₂ CH₂ VI-6  Ph CH₂ C(CH₃)₂ CH₂ VI-7  Ph CHCH₃ CH₂ C(CH₃)₂ VI-8  Ph CHCH₃ CH₂ CHCH₃ VI-9  Ph CHCH₃ CHCH₃ CH₂ VI-10 Ph NCH₃ CO CH₂ VI-11 Ph C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-12 Ph C(CH₃)₂ S C(CH₃)₂ VI-13 Ph C(CH₃)₂ SO C(CH₃)₂ VI-14 Ph C(CH₃)₂ SO₂ C(CH₃)₂ VI-15 Ph C(CH₃)₂ O C(CH₃)₂ VI-16 Ph C(CH₃)₂ NCH₃ C(CH₃)₂ VI-17 Me C(CH₃)₂ CO C(CH₃)₂ VI-18 Me CHCH₃ CH₂ CH₂ VI-19 Me CH₂ CHCH₃ CH₂ VI-20 Me CHCH₃ CHCH₃ CHCH₃ VI-21 Me C(CH₃)₂ CH₂ CH₂ VI-22 Me CH₂ C(CH₃)₂ CH₂ VI-23 Me CHCH₃ CH₂ C(CH₃)₂ VI-24 Me CHCH₃ CH₂ CHCH₃ VI-25 Me CHCH₃ CHCH₃ CH₂ VI-26 Me NCH₃ CO CH₂ VI-27 Me C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-28 Me C(CH₃)₂ S C(CH₃)₂ VI-29 Me C(CH₃)₂ SO C(CH₃)₂ VI-30 Me C(CH₃)₂ SO₂ C(CH₃)₂ VI-31 Me C(CH₃)₂ O C(CH₃)₂ VI-32 Me C(CH₃)₂ NCH₃ C(CH₃)₂ VI-33

C(CH₃)₂ CO C(CH₃)₂ VI-34

CHCH₃ CH₂ CH₂

TABLE 41 Compound No. R¹ A₁ A₂ A₃ VI-35

CH₂ CHCH₃ CH₂ VI-36

CHCH₃ CHCH₃ CHCH₃ VI-37

C(CH₃)₂ CH₂ CH₂ VI-38

CH₂ C(CH₃)₂ CH₂ VI-39

CHCH₃ CH₂ C(CH₃)₂ VI-40

CHCH₃ CH₂ CHCH₃ VI-41

CHCH₃ CHCH₃ CH₂ VI-42

NCH₃ CO CH₂ VI-43

C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-44

C(CH₃)₂ S C(CH₃)₂ VI-45

C(CH₃)₂ SO C(CH₃)₂ VI-46

C(CH₃)₂ SO₂ C(CH₃)₂ VI-47

C(CH₃)₂ O C(CH₃)₂ VI-48

C(CH₃)₂ NCH₃ C(CH₃)₂ VI-49 Ph(4-OMe) C(CH₃)₂ CO C(CH₃)₂ VI-50 Ph(4-OMe) CHCH₃ CH₂ CH₂ VI-51 Ph(4-OMe) CH₂ CHCH₃ CH₂ VI-52 Ph(4-OMe) CHCH₃ CHCH₃ CHCH₃ VI-53 Ph(4-OMe) C(CH₃)₂ CH₂ CH₂ VI-54 Ph(4-OMe) CH₂ C(CH₃)₂ CH₂ VI-55 Ph(4-OMe) CHCH₃ CH₂ C(CH₃)₂ VI-56 Ph(4-OMe) CHCH₃ CH₂ CHCH₃ VI-57 Ph(4-OMe) CHCH₃ CHCH₃ CH₂

TABLE 42 Compound No. R¹ A₁ A₂ A₃ VI-58 Ph(4-OMe) NCH₃ CO CH₂ VI-59 Ph(4-OMe) C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-60 Ph(4-OMe) C(CH₃)₂ S C(CH₃)₂ VI-61 Ph(4-OMe) C(CH₃)₂ SO C(CH₃)₂ VI-62 Ph(4-OMe) C(CH₃)₂ SO₂ C(CH₃)₂ VI-63 Ph(4-OMe) C(CH₃)₂ O C(CH₃)₂ VI-64 Ph(4-OMe) C(CH₃)₂ NCH₃ C(CH₃)₂ VI-65 Ph(2,4-Me₂) C(CH₃)₂ CO C(CH₃)₂ VI-66 Ph(2,4-Me₂) CHCH₃ CH₂ CH₂ VI-67 Ph(2,4-Me₂) CH₂ CHCH₃ CH₂ VI-68 Ph(2,4-Me₂) CHCH₃ CHCH₃ CHCH₃ VI-69 Ph(2,4-Me₂) C(CH₃)₂ CH₂ CH₂ VI-70 Ph(2,4-Me₂) CH₂ C(CH₃)₂ CH₂ VI-71 Ph(2,4-Me₂) CHCH₃ CH₂ C(CH₃)₂ VI-72 Ph(2,4-Me₂) CHCH₃ CH₂ CHCH₃ VI-73 Ph(2,4-Me₂) CHCH₃ CHCH₃ CH₂ VI-74 Ph(2,4-Me₂) NCH₃ CO CH₂ VI-75 Ph(2,4-Me₂) C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-76 Ph(2,4-Me₂) C(CH₃)₂ S C(CH₃)₂ VI-77 Ph(2,4-Me₂) C(CH₃)₂ SO C(CH₃)₂ VI-78 Ph(2,4-Me₂) C(CH₃)₂ SO₂ C(CH₃)₂ VI-79 Ph(2,4-Me₂) C(CH₃)₂ O C(CH₃)₂ VI-80 Ph(2,4-Me₂) C(CH₃)₂ NCH₃ C(CH₃)₂ VI-81

C(CH₃)₂ CO C(CH₃)₂ VI-82

CHCH₃ CH₂ CH₂ VI-83

CH₂ CHCH₃ CH₂ VI-84

CHCH₃ CHCH₃ CHCH₃ VI-85

C(CH₃)₂ CH₂ CH₂ VI-86

CH₂ C(CH₃)₂ CH₂ VI-87

CHCH₃ CH₂ C(CH₃)₂ VI-88

CHCH₃ CH₂ CHCH₃

TABLE 43 Compound No. R¹ A₁ A₂ A₃ VI-89

CHCH₃ CHCH₃ CH₂ VI-90

NCH₃ CO CH₂ VI-91

C(CH₃)₂ C(CH₃)₂ C(CH₃)₂ VI-92

C(CH₃)₂ S C(CH₃)₂ VI-93

C(CH₃)₂ SO C(CH₃)₂ VI-94

C(CH₃)₂ SO₂ C(CH₃)₂ VI-95

C(CH₃)₂ O C(CH₃)₂ VI-96

C(CH₃)₂ NCH₃ C(CH₃)₂ VI-97 Ph(3,4,5-(OMe)₃) C(CH₃)₂ CO C(CH₃)₂

In Formula 1, R¹ is preferably a group selected from a group consisting of a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ halolalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with a substituent group selected from Substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with a substituent group selected from Substituent group α; and a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α, and when the heterocyclic group contains a sulfur atom, it may be oxidized to be present as sulfoxide or sulfone).

In Formula 1, R² is preferably a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may be substituted with a substituent group selected from Substituent group α; and a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom (the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α).

The triazine derivative compounds represented by Formula 1, i.e., the compounds of the invention, and their salts can be produced according to various methods. Representative examples of the production method are given below, but the invention is not limited to them.

<Production Method 1>

The compound represented by following Formula 1a, which is one of the compounds of the invention, can be produced according to the method with the reaction scheme shown below.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z have the same definitions as above and Q represents a leaving group like a halogen atom, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group).

(Process 1)

By reacting the compound of Formula 3 and the compound of Formula 4a in a solvent in the presence of a base, the enolester compound of Formula 5a and/or Formula 5b can be produced.

Herein, the use amount of Formula 4a can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include organic amines like triethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU); metal carbonates like sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate; metal hydrogen carbonates like sodium hydrogen carbonate and potassium hydrogen carbonate; metal carboxylate salts represented by metal acetate salts like sodium acetate, potassium acetate, calcium acetate, and magnesium acetate; metal alkoxides like sodium methoxide, sodium ethoxide, sodium tertiary butoxide, potassium methoxide, and potassium tertiary butoxide; metal hydroxides like sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide, and; metal hydrides like lithium hydride, sodium hydride, potassium hydride, and calcium hydride. The use amount of the base is appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

The solvent that can be used for the present process can be any solvent if it does not inhibit the progress of the reaction. Solvents including nitriles like acetonitrile; ethers like diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, and diglyme; halogenated hydrocarbons like dichloroethane, chloroform, carbon tetrachloride, and tetrachloroethane; aromatic hydrocarbons like benzene, chlorobenzene, nitrobenzene, and toluene; amides like N,N-dimethylformamide and N,N-dimethylacetamide; imidazolinones like 1,3-dimethyl-2-imidazolinone, and; sulfur compounds like dimethyl sulfoxide can be used. Further, their mixture solvent can be also used.

The reaction temperature may be selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. By using a phase transfer catalyst like quaternary ammonium salt, the reaction can be carried out in a two-phase system.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 5a and/or Formula 5b, which is the target compound of the reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

(Process 2)

Compound of Formula 5a and/or Formula 5b can be also produced by reacting the compound of Formula 3 and the compound of Formula 4b with a dehydrating condensing agent in a solvent, in the presence or absence of a base.

The use amount of Formula 4b that is used for the present process can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the dehydrating condensing agent include dicyclohexyl carbodiimide (DCC), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC or WSC), N,N-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride, and 2-chloro-1-pyridinium iodide.

Examples of the base and the solvent which can be used for the present process include those described above for Process 1.

The reaction temperature may be selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

The compound of Formula 5a and/or Formula 5b, which is the target compound of the reaction, can be separated and purified in the same manner as Process 1.

(Process 3)

Compound of Formula 1a can be produced by reacting the compound of Formula 5a and/or Formula 5b produced by Process 1 or Process 2 with a cyano compound in the presence of a base.

Examples of the base which can be used for the present process include those described above for Process 1. The use amount of the base can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 5a and Formula 5b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the cyano compound which can be used for the present process include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 5a and Formula 5b. Preferably, it is from 0.05 to 0.2 mol.

For the present process, a small amount of a phase transfer catalyst like crown ether can be also used.

Examples of the solvent which can be used for the present process include those described above for Process 1. The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Further, according to the present process, compound of Formula 1a can be produced while using Formula 5a and/or Formula 5b produced by Process 1 or Process 2 without any separation.

(Process 4)

Compound of Formula 1a can be also produced by reacting the compound of Formula 3 and the compound of Formula 4c in the presence of a base or a Lewis acid.

The use amount of Formula 4c that is used for the present process can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the Lewis acid include zinc chloride and aluminum chloride.

Examples of the base which can be used for the present process include those described above for Process 1. The use amount of the base that can be used for the present process can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 3. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, compound of Formula 1a, which is produced according to Process 3 or Process 4, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

<Production Method 2>

With regard to Formula 1a produced by Production method 1, the hydroxyl group in the cyclohexane ring can be converted to other substituent group according to the method with the following reaction scheme.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z each have the same definitions as above, R^(4a) represents an amino group, a cyano group, an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxy group, a C₁-C₆ alkoxycarbonyloxy group, a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, a C₂-C₆ alkynyloxy group, a C₃-C₆ cycloalkyloxy group, a cyanomethyleneoxy group, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ alkylcarbonyloxy group, a C₁-C₆ haloalkylcarbonyloxy group, a C₂-C₆ alkenylcarbonyloxy group, a C₂-C₆ halolalkenylcarbonyloxy group, a C₂-C₆ alkynylcarbonyloxy group, a C₂-C₆ halolalkynylcarbonyloxy group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group, a phenyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzyloxy group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylsulfonyloxy group, a phenylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinyl group, a C₁-C₁₀ alkylsulfonyl group, a C₁-C₆ haloalkylthio group, a C₁-C₆ haloalkylsulfinyl group, a C₁-C₆ haloalkylsulfonyl group, a C₂-C₆ alkenylthio group, a C₂-C₆ alkenylsulfinyl group, a C₂-C₆ alkenylsulfonyl group, a C₂-C₆ alkynylthio group, a C₂-C₆ alkynylsulfinyl group, a C₂-C₆ alkynylsulfonyl group, a phenylthio group which may be substituted with a substituent group selected from Substituent group α, a benzylthio group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfinyl group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfinyl group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylamino group, a di(C₁-C₁₀ alkyl)amino group, a C₁-C₆ alkoxycarbonyl amino group, a C₁-C₆ alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], or a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], and X represents a halogen atom).

Specifically, the compound of Formula 1b can be produced by reacting the compound of Formula 1a and a halogenating agent, and Formula 1c can be produced by reacting the compound of Formula 1b and a nucleophilic reagent in the presence of a base.

Examples of the halogenating agent that can be used for preparation of the compound of Formula 1b from the compound of Formula 1a include thionyl chloride, thionyl bromide, phosphorus oxy chloride, phosphorus oxy bromide, phenyltrimethyl ammonium tribromide, and Meldrum's acid tribromide. The use amount of the halogenating agent can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 1a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature may be selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the nucleophilic reagent for the process for obtaining Formula 1e from Formula 1b, which is a compound represented by the formula R^(4a)—H, include alcohols like methanol, ethanol, and benzyl alcohol; mercaptans like methyl mercaptan and ethyl mercaptan; amines like ammonia, methyl amine, and ethyl amine; phenols like p-cresol and phenol; thiophenols like p-chlorothiophenol; a C₁-C₆ alkyl acids like acetic acid, and benzoic acids. The use amount of the nucleophilic reagent can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 1b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include those described above for Process 1 of Production method 1.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1c, which is produced according to this method, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

<Production Method 3>

Compound of Formula 1c can be also produced by the method with the following reaction scheme.

(in the formula, R¹, R², A₁, A₂, A₃, Y and Z each have the same definitions as above, R^(4a) represents a hydroxycarbonyl group, a C₁-C₆ alkoxycarbonyl group, a benzyloxycarbonyl group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a cyanomethylene group, a C₃-C₆ cycloalkyl C₁-C₆ alkyl group, a C₁-C₆ alkylcarbonyl group, a C₁-C₁₀ alkylthiocarbonyl group, a C₁-C₆ haloalkylcarbonyl group, a C₂-C₆ alkenylcarbonyl group, a C₂-C₆ halolalkenylcarbonyl group, a C₂-C₆ alkynylcarbonyl group, a C₂-C₆ halolalkynylcarbonyl group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group, a C₁-C₁₀ alkylsulfonyl group, a phenyl group which may be substituted with a substituent group selected from Substituent group α, a benzyl group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl group which may be substituted with a substituent group selected from Substituent group α, a benzylcarbonyl group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyl group which may be substituted with a substituent group selected from Substituent group α, or a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α]).

Specifically, the compound of Formula 1c can be produced by reacting the compound of Formula 1a and an electrophilic reagent in a solvent in the presence or absence of a base.

The electrophilic reagent indicates a compound represented by the formula R^(4b)-L_(a) (L_(a) represents a leaving group), and examples thereof include C₁-C₆ alkyl halide like methyl iodide and propyl chloride; benzyl halide like benzyl bromide; C₁-C₆ alkylcarbonyl halide like acetyl chloride and propionyl chloride; benzoyl halide like benzoyl chloride; C₂-C₆ alkenylcarbonyl halide like methacryl chloride and crotonyl chloride; C₂-C₆ alkynylcarbonyl halide like 4-pentynoyl chloride; C₁-C₆ alkyl sulfonyl halide like methane sulfonyl chloride and ethane sulfonyl chloride; benzene sulfonyl halide like benzene sulfonyl chloride and p-toluene sulfonyl chloride; and di C₁-C₆ alkyl sulfate ester like dimethyl sulfate and diethyl sulfate. The use amount of the electrophilic reagent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base which can be used for the present process include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1c, which is a target compound of this process, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula 1c of the invention has many tautomers shown below, and they are all included in the invention.

<Production Method 4>

Compound of Formula 1 d can be also produced by the method with the following reaction scheme.

(in the formula, R¹, R², R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, Y and Z each have the same definitions as above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, compound of Formula 1d can be produced by reacting the compound of Formula 6a and the compound of Formula 4a in a solvent, in the presence of a Lewis acid.

The use amount of Formula 4a can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 6a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the Lewis acid that can be used include organo lithium compounds like methyl lithium, ethyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, and benzyl lithium; Grignard's reagent like methyl magnesium iodide and ethyl magnesium bromide; metal compounds like lithium, potassium and sodium; organo copper compounds produced from Grignard's reagent or organometallic compound and monovalent copper salt; alkali metal amides like lithium diisopropyl amide (LDA), and; organic amines like triethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). n-Butyl lithium and lithium diisopropyl amide (LDA) are particularly preferable. The use amount of Lewis acid can be appropriately selected from the range of 0.5 to 10 mol per 1 mol of Formula 5a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1. Diethyl ether and tetrahydrofuran are particularly preferable. The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1d, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula 1d of the invention has many tautomers shown below, and they are all included in the invention.

<Production Method 5>

Compound of Formula 1e can be also produced by the method with the following reaction scheme.

(in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the same definitions as above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5c can be produced by reacting the compound of Formula 6 and the compound of Formula 4a in a solvent in the presence of abase, and the compound of Formula 1e can be produced by reacting the compound of Formula 5c and a cyano compound in the presence of a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5c from Formula 6 can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 6. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base and solvent that can be used include those described above for Process 1 of Production method 1. The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the cyano compound which can be used for the reaction above for obtaining Formula 1e from Formula 5e include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 6. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range of 0.1 to 1.0 mol per 1 mol of Formula 6. Preferably, it is 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1e, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula 1e of the invention has many tautomers shown below, and they are all included in the invention.

<Production Method 6>

Compound of Formula 1g in which the substituent group in the pyrazole ring is modified can be also produced from the compound of Formula 1e by the method with the following reaction scheme.

(in the formula, R¹, R²⁰, R²¹, Y and Z each have the same definitions as above, R^(22a) represents an amino group, a cyano group, an isothiocyanate group, an isocyanate group, a hydroxycarbonyloxy group, a C₁-C₆ alkoxycarbonyloxy group, a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₆ alkoxy group, a C₂-C₆ alkenyloxy group, a C₂-C₆ alkynyloxy group, a C₃-C₆ cycloalkyloxy group, a cyanomethyleneoxy group, a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group, a C₁-C₆ alkylcarbonyloxy group, a C₁-C₆ haloalkylcarbonyloxy group, a C₂-C₆ alkenylcarbonyloxy group, a C₂-C₆ halolalkenylcarbonyloxy group, a C₂-C₆ alkynylcarbonyloxy group, a C₂-C₆ halolalkynylcarbonyloxy group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkoxy group, a phenyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzyloxy group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzylcarbonyloxy group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylsulfonyloxy group, a phenylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfonyloxy group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylthio group, a C₁-C₁₀ alkylsulfinyl group, a C₁-C₁₀ alkylsulfonyl group, a C₁-C₆ haloalkylthio group, a C₁-C₆ haloalkylsulfinyl group, a C₁-C₆ haloalkylsulfonyl group, a C₂-C₆ alkenylthio group, a C₂-C₆ alkenylsulfinyl group, a C₂-C₆ alkenylsulfonyl group, a C₂-C₆ alkynylthio group, a C₂—C alkynylsulfinyl group, a C₂-C₆ alkynylsulfonyl group, a phenylthio group which may be substituted with a substituent group selected from Substituent group α, a benzylthio group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfinyl group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfinyl group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a benzylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₁₀ alkylamino group, a di(C₁-C₁₀ alkyl)amino group, a C₁-C₆ alkoxycarbonyl amino group, a C₁-C₆ alkoxy group substituted with a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], or a heterocyclic oxy group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α], and X represents a halogen atom).

Specifically, the compound of Formula 1f can be produced by reacting the compound of Formula 1e and a halogenating agent and Formula 1g can be produced by reacting it with a nucleophilic reagent.

Examples of the halogenating agent that can be used for the process of producing the compound of Formula 1f from the compound of Formula 1e include thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide, phenyltrimethyl ammonium tribromide, and Meldrum's acid tribromide.

The use amount of the halogenating agent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1. The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

The nucleophilic reagent for the process for obtaining Formula 1 g from Formula 1f is, for example, a compound represented by the formula R^(22a)—H, and examples thereof include alcohols like methanol, ethanol, and benzyl alcohol; mercaptans like methyl mercaptan and ethyl mercaptan; amines like ammonia, methyl amine, and ethyl amine; phenols like p-cresol and phenol; thiophenols like p-chlorothiophenol; C₁-C₆ alkyl acids like acetic acid, and benzoic acids. The use amount of the nucleophilic reagent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1f. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1g, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

<Production Method 7>

Compound of Formula 1g can be also produced by the method with the following reaction scheme.

(in the formula, R¹, R², R²⁰, R²¹, Y and Z each have the same definitions as above, R^(22b) represents a hydroxycarbonyl group, a C₁-C₆ alkoxycarbonyl group, a benzyloxycarbonyl group which may be substituted with a substituent group selected from Substituent group α, a C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂—C alkynyl group, a C₃-C₆ cycloalkyl group, a cyanomethylene group, a C₃-C₆ cycloalkyl C₁-C₆ alkyl group, a C₁-C₆ alkylcarbonyl group, a C₁-C₁₀ alkylthiocarbonyl group, a C₁-C₆ haloalkylcarbonyl group, a C₂-C₆ alkenylcarbonyl group, a C₂-C₆ halolalkenylcarbonyl group, a C₂-C₆ alkynylcarbonyl group, a C₂-C₆ halolalkynylcarbonyl group, a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group, a C₁-C₁₀ alkylsulfonyl group, a phenyl group which may be substituted with a substituent group selected from Substituent group α, a benzyl group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl group which may be substituted with a substituent group selected from Substituent group α, a benzylcarbonyl group which may be substituted with a substituent group selected from Substituent group α, a phenylsulfonyl group which may be substituted with a substituent group selected from Substituent group α, a phenylcarbonyl C₁-C₆ alkyl group which may be substituted with a substituent group selected from Substituent group α, or a heterocyclic group having 3 to 10 carbon atoms and one or more heteroatoms that are the same or different from each other and selected from an oxygen atom, a sulfur atom, and a nitrogen atom [the group may be substituted with one substituent group selected from Substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from Substituent group α]).

Specifically, the compound of Formula 1g can be produced by reacting the compound of Formula 1e and an electrophilic reagent in a solvent, in the presence or absence of a base.

The electrophilic reagent that can be used indicates a compound represented by the formula R^(22b)-L₂ (L₂ represents a leaving group), and examples thereof include C₁-C₆ alkyl halide like methyl iodide and propyl chloride; benzyl halide like benzyl bromide; C₁-C₆ alkylcarbonyl halide like acetyl chloride and propionyl chloride; benzoyl halide like benzoyl chloride; C₂-C₆ alkenylcarbonyl halide like methacryl chloride and crotonyl chloride; C₂-C₆ alkynylcarbonyl halide like 4-pentinoyl chloride; C₁-C₆ alkyl sulfonyl halide methane sulfonyl chloride and ethane sulfonyl chloride; benzene sulfonyl halide like benzene sulfonyl chloride and p-toluene sulfonyl chloride; and di C₁-C₆ alkyl sulfate ester like dimethyl sulfate and diethyl sulfate. The use amount of the electrophilic reagent can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base and the solvent which can be used for the present process include those described above for Process 1 of Production method 1.

The use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1e. Preferably, it is from 1.0 to 1.2 mol.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C.

The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1g, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

<Production Method 8>

Compound of Formula 1h can be also produced by the method with the following reaction scheme.

(in the formula, R¹, R², R²⁴, R²⁵, Y and Z each have the same definitions as above and Q represents a leaving group like a halogen atom, alkylcarbonyloxy group, an alkoxycarbonyloxy group, a haloalkylcarbonyloxy group, a haloalkoxycarbonyloxy group, a benzoyloxy group, a pyridyl group, and an imidazolyl group, as described above).

Specifically, the compound of Formula 5d can be produced by reacting the compound of Formula 7 and the compound of Formula 4a in a solvent, in the presence of a base, and the compound of Formula 1h can be produced by reacting the compound of Formula 5d and a cyano compound in the presence of a base.

In the above reaction, use amount of Formula 4a for preparing Formula 5d from Formula 7 can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 7. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described above for Process 1 of Production method 1.

Examples of the cyano compound which can be used for the reaction above for obtaining Formula 1h from Formula 5d include potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide. The use amount of the cyano compound can be appropriately selected from the range of 0.01 to 1.0 mol per 1 mol of Formula 5d. Preferably, it is 0.05 to 0.2 mol.

Examples of the base that can be used include those described above for Process 1 of Production method 1. The use amount of the base can be appropriately selected from the range of 0.1 to 1.0 mol per 1 mol of Formula 5d. Preferably, it is 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1h, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Formula 1h of the invention has many tautomers shown below, and they are all included in the invention.

<Production Method 9>

Compound of Formula 1i can be produced by the method with the following reaction scheme.

(in the formula, R¹, R², R²⁴, Y and Z each have the same definitions as above, R²⁵ represents a C₁-C₆ alkoxycarbonyl group, R²⁶ represents an alkoxy group, a haloalkoxy group, a cycloalkoxy group, or a dimethylamino group, and R²⁷ represents an alkyl group or a benzyl group).

(Process 1)

In this process, Formula 8a can be prepared by reacting Formula 1h and acid with or without using a solvent.

Examples of the acid that can be used for the present process include sulfonic acids like p-toluene sulfonic acid. Use amount of the acid can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 1h. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 2)

By reacting Formula 8a and an ortho formic acid ester compound in N,N-dimethylacetamide dimethyl acetal compound or acetic anhydride, Formula 8b can be obtained. Use amount of N,N-dimethylacetamide dimethyl acetal and ortho formic acid ester can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is from 1.0 to 3.0 mol.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 150° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 3)

Formula 8c can be obtained by reacting Formula 8a and carbon disulfide, and without isolation, adding with alkyl halide like methyl iodide or benzyl halide like benzyl bromide. Use amount of carbon disulfide can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is from 1.0 to 1.2 mol. Use amount of the halide can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8a. Preferably, it is 2.0 to 2.4 mol. Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Process 4 & Process 5)

Formula 1i can be obtained by reacting Formula 8b or Formula 8c obtained from Process 2 or Process 3 above and hydroxylamine chloride in a solvent.

Use amount of hydroxylamine chloride can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 8b or Formula 8c. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20′C to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 1i, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Hereinbelow, a method of producing synthetic intermediates of the compounds of the invention is given.

<Production Method 10>

Compound of Formula 3b can be produced by the method with the following reaction scheme.

(in the formula, R¹, R², Y and Z each have the same definitions as above, R³⁰ represents a phenyl group or an alkyl group, and M represents sodium, potassium or trimethylsilyl).

(Route a)

Specifically, compound of Formula 10 can be obtained by reacting the compound of Formula 9 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 10 and the compound of Formula 11 or the compound of Formula 12 in the presence of a base.

Use amount of diethyl ketomalonate for the process of producing Formula 10 from Formula 9 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the compound of Formula 11 or the compound of Formula 12 for the process of producing Formula 13a from Formula 10 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 10. Preferably, it is from 1.0 to 1.2 mol.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 10. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route b)

Specifically, compound of Formula 15 can be obtained by reacting the compound of Formula 9 and the compound of Formula 14. In addition, compound of Formula 16 can be obtained by reacting the compound of Formula 15 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 16 and an alkylating agent in the presence of a base.

Use amount of the compound of Formula 14 for the process of producing Formula 15 from Formula 9 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula 16 from Formula 15 can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 15. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the alkylating agent for the process of producing Formula 13a from Formula 16 can be appropriately selected from the range of 1.0 to 3.0 mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.5 mol.

Examples of the alkylating agent that can be used include alkyl sulfates like dimethyl sulfate and diethyl sulfate; alkyl halides like methyl iodide, ethyl iodide, benzyl chloride, benzyl bromide, propargyl bromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acid esters like ethoxyethyl p-toluene sulfonate and cyclopentylmethane sulfonate.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 16. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route c)

Specifically, compound of Formula 17a can be obtained by reacting the compound of Formula 11a and hydrazine hydrate. In addition, compound of Formula 18 can be obtained by reacting the compound of Formula 17 and diethyl ketomalonate. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 18 and an alkylating agent in the presence of a base.

Use amount of hydrazine hydrate for the process of producing Formula 17a from Formula 11a can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula 18 from Formula 17a can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 17a. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1,

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of the alkylating agent for the process of producing Formula 13a from Formula 18 can be appropriately selected from the range of 1.0 to 3.0 mol per 1 mol of Formula 18. Preferably, it is from 1.0 to 1.5 mol.

Examples of the alkylating agent that can be used include alkyl sulfates like dimethyl sulfate and diethyl sulfate; alkyl halides like methyl iodide, ethyl iodide, benzyl chloride, benzyl bromide, propargyl bromide, ethyl bromoacetate, and chloroacetonitrile, and; sulfonic acid esters like ethoxyethyl p-toluene sulfonate and cyclopentylmethane sulfonate.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1. Use amount of the base can be appropriately selected from the range of 0.1 to 10 mol per 1 mol of Formula 18. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route d)

Specifically, compound of Formula 17b can be obtained by reacting the compound of Formula 11a and the compound of Formula 9. In addition, compound of Formula 13a can be obtained by reacting the compound of Formula 17b and diethyl ketomalonate, using an acid or a base depending on the condition.

Use amount of the compound of Formula 9 for the process of producing Formula 17b from Formula 11a can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 9. Preferably, it is from 1.0 to 1.2 mol.

Examples of the acid that can be used include organic acids represented by organic sulfonic acid like p-toluene sulfonic acid, methane sulfonic acid, and benzene sulfonic acid; hydrogen halide acids represented by hydrochloric acid and hydrogen bromic acid, and; inorganic acids like sulfuric acid and phosphoric acid. These acids can be used either singly or in combination of two or more.

Examples of the base that can be used for the present process include those described above for Process 1 of Production method 1.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Use amount of diethyl ketomalonate for the process of producing Formula 13a from Formula 17b can be appropriately selected from the range of 1.0 to 1.5 mol per 1 mol of Formula 17b. Preferably, it is from 1.0 to 1.2 mol.

Examples of the solvent that can be used for the present process include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

Examples of the acid include organic acids like p-toluene sulfonic acid.

Examples of the base include organic bases like triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and inorganic bases like sodium hydride, sodium methoxide, and sodium ethoxide.

After the completion of the reaction, the compound of Formula 13a, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

(Route e)

Specifically, compound of Formula 3b can be obtained by hydrolyzing the compound of Formula 13a.

With regard to the process of obtaining the compound of Formula 3b from the compound of Formula 13a, the production can be carried out by hydrolysis in water, organic solvent, or a mixture solvent in the presence of an acid or a base.

Examples of the base that can be used include those described above for Process 1 of Production method 1.

Use amount of the base can be appropriately selected from the range of 0.01 to 100 mol per 1 mol of Formula 13a. Preferably, it is 0.1 to 10 mol.

Examples of the acid that can be used include inorganic acids like hydrochloric acid, hydrobromic acid, and sulfuric acid, and organic acids like acetic acid and trifluoroacetic acid.

Use amount of the acid can be appropriately selected from the range of 1 mol to excess amount per 1 mol of Formula 13a. Preferably, it is from 1 to 100 mol.

Examples of the organic solvent that can be used include a mixture solvent of water and an organic solvent. Examples of the organic solvent include alcohols like methanol and ethanol, ether like tetrahydrofuran, ketones like acetone and methyl isobutyl ketone, amides like N,N-dimethyl formamide and N,N-dimethyl acetamide, sulfur compounds like dimethyl sulfoxide and sulfolane, acetonitrile, and their mixture.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 13a. Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

(Route f)

Specifically, compound of Formula 13b can be obtained by reacting the compound of Formula 13a and a sulfurizing agent. In addition, the compound of Formula 3b can be obtained by hydrolyzing the compound of Formula 13b.

Use amount of the compound of the sulfurizing agent for the process of producing Formula 13b from Formula 13a can be appropriately selected from the range of 1.0 to 8.0 mol per 1 mol of Formula 13a. Preferably, it is from 1.0 to 4.0 mol.

Examples of the sulfurizing agent that can be used include diphosphorus pentoxide and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide.

Use amount of the compound of the sulfurizing agent can be appropriately selected from the range of 1.0 to 8.0 mol per 1 mol of Formula 13a. Preferably, it is 0.1 to 4.0 mol.

Examples of the solvent that can be used include those described above for Process 1 of Production method 1.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

With regard to the process of obtaining the compound of Formula 3b from the compound of Formula 13b, the production can be carried out by hydrolysis in water, organic solvent, or a mixture solvent in the presence of an acid or a base.

Examples of the base that can be used include those described above for Process 1 of Production method 1.

Use amount of the base can be appropriately selected from the range of 0.01 to 100 mol per 1 mol of Formula 13b. Preferably, it is 0.1 to 10 mol.

Examples of the acid that can be used include inorganic acids like hydrochloric acid, hydrobromic acid, and sulfuric acid, and organic acids like acetic acid and trifluoroacetic acid.

Use amount of the acid can be appropriately selected from the range of 1 mol to excess amount per 1 mol of Formula 13b. Preferably, it is from 1 to 100 mol.

Examples of the organic solvent that can be used include a mixture solvent of water and an organic solvent. Examples of the organic solvent include alcohols like methanol and ethanol, ether like tetrahydrofuran, ketones like acetone and methyl isobutyl ketone, amides like N,N-dimethyl formamide and N,N-dimethyl acetamide, sulfur compounds like dimethyl sulfoxide and sulfolane, acetonitrile, and their mixture.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 13b. Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 3b, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

<Intermediate Synthesis Method 1>

Compound of Formula 3a can be produced according to the method with the following reaction scheme.

(in the formula, R¹, R², Y and Z each have the same definitions as above and X represents a chlorine or a bromine).

Specifically, Formula 3a can be produced by reacting Formula 3b and an appropriate halogenating agent with or without a solvent.

Examples of the halogenating agent that can be used include oxalyl chloride and thionyl chloride.

Use amount of the halogenating agent can be appropriately selected from the range of 0.01 to 20 mol per 1 mol of Formula 3b. Preferably, it is from 1 to 10 mol.

Examples of the solvent include halogenated hydrocarbons like dichloromethane and chloroform, ethers like diethyl ether and tetrahydrofuran, and aromatic hydrocarbons like benzene and toluene.

Use amount of the solvent is 0.01 to 100 L per 1 mol of Formula 3b. Preferably, it is 0.1 to 10 L.

The reaction temperature is selected from the range of from −20° C. to the boiling point of an inert solvent used. Preferably, the reaction is carried out in the range of from 0° C. to 100° C. The reaction time varies depending on the reaction temperature, the reaction substrates, the reaction amount, etc. In general, it is from 10 minutes to 48 hours.

After the completion of the reaction, the compound of Formula 3a, i.e., the target compound of this reaction, can be collected from the reaction system by general method, and if necessary, purified by a process like column chromatography and recrystallization.

Examples of the production intermediates [13a] and [3b], that can be described for the Production method 10, are shown in Table 44 to Table 67.

TABLE 44

Compound No. R¹ R² Y Z IV-1  Me Me O O IV-2  Et Me O O IV-3  Pr-n Me O O IV-4  Pr-i Me O O IV-5  Bu-n Me O O IV-6  Bu-i Me O O IV-7  Bu-s Me O O IV-8  Bu-t Me O O IV-9  Hex-n Me O O IV-10 CH₂CF₃ Me O O IV-11 CH₂CH═CH₂ Me O O IV-12 CH₂C(Me)═CH₂ Me O O IV-13 CH₂CH₂CH═CMe₂ Me O O IV-14 CH₂C≡CH Me O O IV-15 CH₂C≡CCH₃ Me O O IV-16 Pr-c Me O O IV-17 Bu-c Me O O IV-18 Pen-c Me O O IV-19 Hex-c Me O O IV-20 CH₂Pr-c Me O O IV-21 CH₂Bu-c Me O O IV-22 CH₂Pen-c Me O O IV-23 CH₂Hex-c Me O O IV-24 CH₂CH═CCl₂ Me O O IV-25 CH₂CCl═CHCl Me O O IV-26 CH₂CH₂CH═CCl₂ Me O O IV-27 CH₂CH₂C(Me)═CF₂ Me O O IV-28 CH₂CH₂CH₂CH₂C(Me)═CF₂ Me O O IV-29 CH₂CH═CF₂ Me O O IV-30 CH₂CH₂OMe Me O O IV-31 CH₂CH₂OEt Me O O IV-32 CH(Me)CH₂OMe Me O O IV-33 CH₂CH₂OCH₂CH₂OMe Me O O IV-34 CH₂CH₂OPr-n Me O O IV-35 CH₂CH₂OPr-i Me O O IV-36 CH₂CH₂OPr-c Me O O

TABLE 45 Compound No. R¹ R² Y Z IV-37 CH₂CH₂OBu-c Me O O IV-38 CH₂CH₂OPen-c Me O O IV-39 CH₂CH₂OHex-c Me O O IV-40 CH₂CH₂OCH₂CF₃ Me O O IV-41 CH₂CH₂CH₂OMe Me O O IV-42 CH═CHMe Me O O IV-43 CH₂SMe Me O O IV-44 CH₂SPr-n Me O O IV-45 CH₂CH₂SMe Me O O IV-46 CH₂SOMe Me O O IV-47 CH₂SO₂Me Me O O IV-48 CH₂CH₂CH₂SMe Me O O IV-49 CH₂CH₂CH₂SO₂Me Me O O IV-50 Ph Me O O IV-51 Ph(2-Cl) Me O O IV-52 Ph(3-Cl) Me O O IV-53 Ph(4-Cl) Me O O IV-54 Ph(2-F) Me O O IV-55 Ph(3-F) Me O O IV-56 Ph(4-F) Me O O IV-57 Ph(2-Me) Me O O IV-58 Ph(3-Me) Me O O IV-59 Ph(4-Me) Me O O IV-60 Ph(2-OMe) Me O O IV-61 Ph(3-OMe) Me O O IV-62 Ph(4-OMe) Me O O IV-63 Ph(2-CF₃) Me O O IV-64 Ph(3-CF₃) Me O O IV-65 Ph(4-CF₃) Me O O IV-66 Ph(2-NO₂) Me O O IV-67 Ph(3-NO₂) Me O O IV-68 Ph(4-NO₂) Me O O IV-69 Ph(2-OCF₃) Me O O IV-70 Ph(3-OCF₃) Me O O IV-71 Ph(4-OCF₃) Me O O IV-72 Ph(2-CN) Me O O IV-73 Ph(3-CN) Me O O IV-74 Ph(4-CN) Me O O IV-75 Ph(3,4-F₂) Me O O

TABLE 46 Compound No. R¹ R² Y Z IV-76 Ph(3,5-F₂) Me O O IV-77 Ph(2,3-F₂) Me O O IV-78 Ph(2,4-F₂) Me O O IV-79 Ph(2,5-F₂) Me O O IV-80 Ph(2,6-F₂) Me O O IV-81 Ph(3,4-Cl₂) Me O O IV-82 Ph(3,5-Cl₂) Me O O IV-83 Ph(2,3-Cl₂) Me O O IV-84 Ph(2,4-Cl₂) Me O O IV-85 Ph(2,5-Cl₂) Me O O IV-86 Ph(2,6-Cl₂) Me O O IV-87 Ph(3,4-Me₂) Me O O IV-88 Ph(3,5-Me₂) Me O O IV-89 Ph(2,3-Me₂) Me O O IV-90 Ph(2,4-Me₂) Me O O IV-91 Ph(2,5-Me₂) Me O O IV-92 Ph(2,6-Me₂) Me O O IV-93 Ph(3,4-(OMe)₂) Me O O IV-94 Ph(3,5-(OMe)₂) Me O O IV-95 Ph(2,3-(OMe)₂) Me O O IV-96 Ph(2,4-(OMe)₂) Me O O IV-97 Ph(2,5-(OMe)₂) Me O O IV-98 Ph(2,6-(OMe)₂) Me O O IV-99 Ph(3-F-4-OMe) Me O O IV-100 Ph(3-F-5-OMe) Me O O IV-101 Ph(2-F-3-OMe) Me O O IV-102 Ph(2-F-4-OMe) Me O O IV-103 Ph(2-F-5-OMe) Me O O IV-104 Ph(2-F-6-OMe) Me O O IV-105 Ph(3-F-4-Me) Me O O IV-106 Ph(3-F-5-Me) Me O O IV-107 Ph(2-F-3-Me) Me O O IV-108 Ph(2-F-4-Me) Me O O IV-109 Ph(2-F-5-Me) Me O O IV-110 Ph(2-F-6-Me) Me O O IV-111 Ph(3-OMe-4-F) Me O O IV-112 Ph(2-OMe-3-F) Me O O IV-113 Ph(2-OMe-4-F) Me O O IV-114 Ph(2-OMe-5-F) Me O O

TABLE 47 Compound No. R¹ R² Y Z IV-115 Ph(3-Me-4-F) Me O O IV-116 Ph(2-Me-3-F) Me O O IV-117 Ph(2-Me-4-F) Me O O IV-118 Ph(2-Me-5-F) Me O O IV-119 Ph(3-Cl-4-OMe) Me O O IV-120 Ph(3-Cl-5-OMe) Me O O IV-121 Ph(2-Cl-3-OMe) Me O O IV-122 Ph(2-Cl-4-OMe) Me O O IV-123 Ph(2-Cl-5-OMe) Me O O IV-124 Ph(2-Cl-6-OMe) Me O O IV-125 Ph(3-Cl-4-Me) Me O O IV-126 Ph(3-Cl-5-Me) Me O O IV-127 Ph(2-Cl-3-Me) Me O O IV-128 Ph(2-Cl-4-Me) Me O O IV-129 Ph(2-Cl-5-Me) Me O O IV-130 Ph(2-Cl-6-Me) Me O O IV-131 Ph(3-OMe-4-Cl) Me O O IV-132 Ph(2-OMe-3-Cl) Me O O IV-133 Ph(2-OMe-4-Cl) Me O O IV-134 Ph(2-OMe-5-Cl) Me O O IV-135 Ph(3-Me-4-Cl) Me O O IV-136 Ph(2-Me-3-Cl) Me O O IV-137 Ph(2-Me-4-Cl) Me O O IV-138 Ph(2-Me-5-Cl) Me O O IV-139 Ph(3-F-4-Cl) Me O O IV-140 Ph(3-F-5-Cl) Me O O IV-141 Ph(2-F-3-Cl) Me O O IV-142 Ph(2-F-4-Cl) Me O O IV-143 Ph(2-F-5-Cl) Me O O IV-144 Ph(2-F-6-Cl) Me O O IV-145 Ph(3-Cl-4-F) Me O O IV-146 Ph(2-Cl-3-F) Me O O IV-147 Ph(2-Cl-4-F) Me O O IV-148 Ph(2-Cl-5-F) Me O O IV-149 Ph(3-Me-4-OMe) Me O O IV-150 Ph(3-Me-5-OMe) Me O O IV-151 Ph(2-Me-3-OMe) Me O O IV-152 Ph(2-Me-4-OMe) Me O O IV-153 Ph(2-Me-5-OMe) Me O O

TABLE 48 Compound No. R¹ R² Y Z IV-154 Ph(2-Me-6-OMe) Me O O IV-155 Ph(3-OMe-4-Me) Me O O IV-156 Ph(2-OMe-3-Me) Me O O IV-157 Ph(2-OMe-4-Me) Me O O IV-158 Ph(2-OMe-5-Me) Me O O IV-159 Ph(3-CN-4-OMe) Me O O IV-160 Ph(3-OMe-4-CN) Me O O IV-161 Ph(3-Me-4-CN) Me O O IV-162 Ph(3-CN-4-Me) Me O O IV-163 Ph(3-NO₂-4-OMe) Me O O IV-164 Ph(3-OMe-4-NO₂) Me O O IV-165 Ph(3-Me-4-NO₂) Me O O IV-166 Ph(3-NO₂-4-Me) Me O O IV-167 Ph(3,5-F₂-5-OMe) Me O O IV-168 Ph(3,5-F₂-5-OMe) Me O O IV-169 Ph(3,4,5-(OMe)₃) Me O O IV-170

Me O O IV-171

Me O O IV-172

Me O O IV-173

Me O O IV-174

Me O O IV-175

Me O O IV-176

Me O O IV-177

Me O O

TABLE 49 Compound No. R¹ R² Y Z IV-178

Me O O IV-179

Me O O IV-180

Me O O IV-181

Me O O IV-182

Me O O IV-183

Me O O IV-184

Me O O IV-185

Me O O IV-186

Me O O IV-187

Me O O IV-188

Me O O IV-189

Me O O IV-190

Me O O IV-191

Me O O

TABLE 50 Compound No. R¹ R² Y Z IV-192

Me O O IV-193

Me O O IV-194

Me O O IV-195

Me O O IV-196

Me O O IV-197

Me O O IV-198

Me O O IV-199

Me O O IV-200

Me O O IV-201

Me O O IV-202

Me O O IV-203

Me O O IV-204

Me O

TABLE 51 Compound No. R¹ R² Y Z IV-205 CH₂Ph Me O O IV-206 CH₂CH₂Ph Me O O IV-207 CH₂CH₂CH₂Ph Me O O IV-208 CH₂CH═CHPh Me O O IV-209 CH₂C≡CPh Me O O IV-210 CH₂CH═NOMe Me O O IV-211 CH₂CH═NOEt Me O O IV-212 CH₂CH═NOPr-n Me O O IV-213 CH₂CH═NOPh Me O O IV-214 CH₂CH(OMe)₂ Me O O IV-215 CH₂CHO Me O O IV-216 NH₂ Me O O IV-217 NHMe Me O O IV-218 NHEt Me O O IV-219 NHPr-n Me O O IV-220 NHPr-i Me O O IV-221 NHBu-n Me O O IV-222 NHBu-i Me O O IV-223 NHBu-s Me O O IV-224 NHCH₂Pr-c Me O O IV-225 NHPen-n Me O O IV-226 NHHex-n Me O O IV-227 NHCH₂CH₂CH₂Cl Me O O IV-228 NHCH₂CH₂CH₂F Me O O IV-229 NHCH₂CH₂OMe Me O O IV-230 NMe₂ Me O O IV-231 NEt₂ Me O O IV-232 N(Pr-n)₂ Me O O IV-233 N(Bu-n)₂ Me O O IV-234 N(Me)Et Me O O IV-235 N(Me)CH₂CH₂OMe Me O O IV-236 NHPh Me O O IV-237 NHCH₂Ph Me O O IV-238 N═CMe₂ Me O O IV-239 N═CEt₂ Me O O IV-240 N═CHNMe₂ Me O O IV-241 NHC(═O)Me Me O O IV-242 N[C(═O)Me]₂ Me O O IV-243 NHC(═O)OMe Me O O IV-244 N[C(═O)OMe]₂ Me O O IV-245 NHSO₂Me Me O O

TABLE 52 Compound No. R¹ R² Y Z IV-246 NHSO₂Ph Me O O IV-247 NHSO₂CH₂Ph Me O O IV-248 OMe Me O O IV-249 OEt Me O O IV-250 OPr-n Me O O IV-251 OPr-i Me O O IV-252 OCH₂Pr-c Me O O IV-253 OCH₂Cl Mc O O IV-254 OCHCl₂ Me O O IV-255 OCCl₃ Me O O IV-256 OCH₂F Me O O IV-257 OCHF₂ Me O O IV-258 OCF₃ Me O O IV-259 Ph Et O O IV-260 Ph Pr-i O O IV-261 Ph CHF₂ O O IV-262 Ph Ph O O IV-263 Ph Me O S IV-264 Ph Me S S IV-265 Me Me O S IV-266 Me Me S S IV-267 Ph Me O O IV-268 Ph(4-OEt) Me O O IV-269 Ph(2-Ph) Me O O IV-270 Ph(3-Ph) Me O O IV-271 Ph(4-Ph) Me O O IV-272

Me O O IV-273

Me O O IV-274 Me

O O IV-275 Et

O O IV-276 Me O O

TABLE 53 Compound No. R¹ R² Y Z IV-277

Me O O IV-278

Me O O IV-279

Me O O IV-280

Me O O IV-281

Me O O IV-282 Ph(2-Me-4-Br) Me O O IV-283 Ph(2-Me-4-I) Me O O IV-284 Ph(2-Me-4-CF₃) Me O O IV-285 Ph(2-Me-4-OCF₃) Me O O IV-286 Ph(2-Pr-i) Me O O IV-287

Me O O IV-288 Ph(2-Et) Me O O IV-289

Me O O IV-290

Me O O IV-291

Me O S IV-292

Me O O IV-293

Me O O IV-294 CH₂COOBu-t Me O O IV-295 (C₇H₁₄)CH₃ Me O O IV-296 (C₉H₁₈)CH₃ Me O O IV-297 Ph(2-F,4-Cl,5-OMe) Me O O IV-298 Ph(2,3,4-(OMe)₃) Me O O IV-299 Ph(3,5-Cl₂-4-OMe) Me O O IV-300 Ph(3,5-Cl₂-4-SMe) Me O O

TABLE 54 Compound No. R¹ R² Y Z IV-301 Ph(3,5-Cl₂-4-SO₂Me) Me O O IV-302 Ph(3,4,5-F₃) Me O O IV-303

Me O O IV-304

Me O O IV-305

Me O O IV-306 Bu-n

O O IV-307 CH₂CH(CH₃)₂

O O IV-308 Ph Pen-n O O IV-309 H Me O O IV-310 CH₂C≡CF Me O O IV-311

Me O O IV-312

M e O O IV-313 CH₂NH₂ Me O O IV-314 CH₂NO₂ Mc O O IV-315 CH₂NHCH₃ Me O O IV-316 CH₂N(CH₃)₂ Me O O IV-317 CH₂SCH₂CF₃ Me O O IV-318 CH₂SOCH₂CF₃ Me O O IV-319 CH₂SO₂CH₂CF₃ Me O O IV-320 CH₂OH Me O O IV-321 CH₂OBn Me O O IV-322 CH₂OCH₂Pr-c Me O O IV-323 CH₂OPh Me O O IV-324 CH₂SPh Me O O IV-325 CH₂SOPh Me O O IV-326 CH₂SO₂Ph Me O O IV-327 CH₂CON(CH₃)₂ Me O O IV-328 CH₂COCH₃ Me O O IV-329 CH₂OCOCH₃ Me O O

TABLE 55 Compound No. R¹ R² Y Z IV-330 CH₂ON═CHCH₃ Me O O IV-331 C₃H₄OC₂H₄SCH₃ Me O O IV-332 C₂H₄OC₂H₄SOCH₃ Me O O IV-333 C₂H₄OC₂H₄SO₂CH₃ Me O O IV-334 CH₂OCH₂CN Me O O IV-335 CH₂CN Me O O IV-336 OCH₂CH═CH₂ Me O O IV-337 OCH₂C≡CH Me O O IV-338 OPr-c Me O O IV-339

Me O O IV-340

Me O O IV-341

Me O O IV-342

Me O O IV-343

Me O O IV-344 Ph H O O IV-345 Ph CH₂CH═CH₂ O O IV-346 Ph CH₂C≡CH O O IV-347 Ph Pr-c O O IV-348 Ph CH₂CH═CF₂ O O IV-349 Ph CH₂C≡CF O O IV-350 Ph C₂H₄OCH₃ O O IV-351 Ph C₂H₄OC₂H₅ O O IV-352 Ph CH(Me)OEt O O IV-353 Ph CH₂OPr-c O O IV-354 Ph CH(OCH₃)₂ O O IV-355 Ph CH₂Ph O O IV-356 Ph CH═CH—Ph O O IV-357 Ph C≡C—Ph O O

TABLE 56

Compound No. R¹ R² Y Z V-1  Me Me O O V-2  Et Me O O V-3  Pr-n Me O O V-4  Pr-i Me O O V-5  Bu-n Me O O V-6  Bu-i Me O O V-7  Bu-s Me O O V-8  Bu-t Me O O V-9  Hex-n Me O O V-10 CH₂CF₃ Me O O V-11 CH₂OH═CH₂ Me O O V-12 CH₂C(Me)═CH₂ Me O O V-13 CH₂CH₂CH═CMe₂ Me O O V-14 CH₂C≡CH Me O O V-15 CH₂C≡CCH₃ Me O O V-16 Pr-c Me O O V-17 Bu-c Me O O V-18 Pen-c Me O O V-19 Hex-c Me O O V-20 CH₂Pr-c Me O O V-21 CH₂Bu-c Me O O V-22 CH₂Pen-c Me O O V-23 CH₂Hex-c Me O O V-24 CH₂CH═CCl₂ Me O O V-25 CH₂CCl═CHCl Me O O V-26 CH₂CH₂CH═CCl₂ Me O O V-27 CH₂CH₂C(Me)═CF₂ Me O O V-28 CH₂CH₂CH₂CH₂CMe)═CF₂ Me O O V-29 CH₂CH═CF₂ Me O O V-30 CH₂CH₂OMe Me O O V-31 CH₂CH₂OEt Me O O V-32 CH(Me)CH₂OMe Me O O V-33 CH₂CH₂OCH₂CH₂OMe Me O O V-34 CH₂CH₂OPr-n Me O O V-35 CH₂CH₂OPr-i Me O O V-36 CH₂CH₂OPr-c Me O O V-37 CH₂CH₂OBu-c Me O O V-38 CH₂CH₂OPen-c Me O O

TABLE 57 Compound No. R¹ R² Y Z V-39 CH₂CH₂OHex-c Me O O V-40 CH₂CH₂OCH₂CF₃ Me O O V-41 CH₂CH₂CH₂OMe Me O O V-42 CH═CHMe Me O O V-43 CH₂SMe Me O O V-44 CH₂SPr-n Me O O V-45 CH₂CH₂SMe Me O O V-46 CH₂SOMe Me O O V-47 CH₂SO₂Me Me O O V-48 CH₂CH₂CH₂SMe Me O O V-49 CH₂CH₂CH₂SO₂Me Me O O V-50 Ph Me O O V-51 Ph(2-Cl) Me O O V-52 Ph(3-Cl) Me O O V-53 Ph(4-Cl) Me O O V-54 Ph(2-F) Me O O V-55 Ph(3-F) Me O O V-56 Ph(4-F) Me O O V-57 Ph(2-Me) Me O O V-58 Ph(3-Me) Me O O V-59 Ph(4-Me) Me O O V-60 Ph(2-OMe) Me O O V-61 Ph(3-OMe) Me O O V-62 Ph(4-OMe) Me O O V-63 Ph(2-CF₃) Me O O V-64 Ph(3-CF₃) Me O O V-65 Ph(4-CF₃) Me O O V-66 Ph(2-NO₂) Me O O V-67 Ph(3-NO₂) Me O O V-68 Ph(4-NO₂) Me O O V-69 Ph(2-OCF₃) Me O O V-70 Ph(3-OCF₃) Me O O V-71 Ph(4-OCF₃) Me O O V-72 Ph(2-CN) Me O O V-73 Ph(3-CN) Me O O V-74 Ph(4-CN) Me O O V-75 Ph(3,4-F₂) Me O O V-76 Ph(3,5-F₂) Me O O V-77 Ph(2,3-F₂) Me O O V-78 Ph(2,4-F₂) Me O O

TABLE 58 Compound No. R¹ R² Y Z V-79 Ph(2,5-F₂) Me O O V-80 Ph(2,6-F₂) Me O O V-81 Ph(3,4-Cl₂) Me O O V-82 Ph(3,5-Cl₂) Me O O V-83 Ph(2,3-Cl₂) Me O O V-84 Ph(2,4-Cl₂) Me O O V-85 Ph(2,5-Cl₂) Me O O V-86 Ph(2,6-Cl₂) Me O O V-87 Ph(3,4-Me₂) Me O O V-88 Ph(3,5-Me₂) Me O O V-89 Ph(2,3-Me₂) Me O O V-90 Ph(2,4-Me₂) Me O O V-91 Ph(2,5-Me₂) Me O O V-92 Ph(2,6-Me₂) Me O O V-93 Ph(3,4-(OMe)₂) Me O O V-94 Ph(3,5-(OMe)₂) Me O O V-95 Ph(2,3-(OMe)₂) Me O O V-96 Ph(2,4-(OMe)₂) Me O O V-97 Ph(2,5-(OMe)₂) Me O O V-98 Ph(2,6-(OMe)₂) Me O O V-99 Ph(3-F-4-OMe) Me O O V-100 Ph(3-F-5-OMe) Me O O V-101 Ph(2-F-3-OMe) Me O O V-102 Ph(2-F-4-OMe) Me O O V-103 Ph(2-F-5-OMe) Me O O V-104 Ph(2-F-6-OMe) Me O O V-105 Ph(3-F-4-Me) Me O O V-106 Ph(3-F-5-Me) Me O O V-107 Ph(2-F-3-Me) Me O O V-108 Ph(2-F-4-Me) Me O O V-109 Ph(2-F-5-Me) Me O O V-110 Ph(2-F-6-Me) Me O O V-111 Ph(3-OMe-4-F) Me O O V-112 Ph(2-OMe-3-F) Me O O V-113 Ph(2-OMe-4-F) Me O O V-114 Ph(2-OMe-5-F) Me O O V-115 Ph(3-Me-4-F) Me O O V-116 Ph(2-Me-3-F) Me O O V-117 Ph(2-Me-4-F) Me O O

TABLE 59 Compound No. R¹ R² Y Z V-118 Ph(2-Me-5-F) Me O O V-119 Ph(3-Cl-4-OMe) Me O O V-120 Ph(3-Cl-5-OMe) Me O O V-121 Ph(2-Cl-3-OMe) Me O O V-122 Ph(2-Cl-4-OMe) Me O O V-123 Ph(2-Cl-5-OMe) Me O O V-124 Ph(2-Cl-6-OMe) Me O O V-125 Ph(3-Cl-4-Me) Me O O V-126 Ph(3-Cl-5-Me) Me O O V-127 Ph(2-Cl-3-Me) Me O O V-128 Ph(2-Cl-4-Me) Me O O V-129 Ph(2-Cl-5-Me) Me O O V-130 Ph(2-Cl-6-Me) Me O O V-131 Ph(3-OMe-4-Cl) Me O O V-132 Ph(2-OMe-3-Cl) Me O O V-133 Ph(2-OMe-4-Cl) Me O O V-134 Ph(2-OMe-5-Cl) Me O O V-135 Ph(3-Me-4-Cl) Me O O V-136 Ph(2-Me-3-Cl) Me O O V-137 Ph(2-Me-4-Cl) Me O O V-138 Ph(2-Me-5-Cl) Me O O V-139 Ph(3-F-4-Cl) Me O O V-140 Ph(3-F-5-Cl) Me O O V-141 Ph(2-F-3-Cl) Me O O V-142 Ph(2-F-4-Cl) Me O O V-143 Ph(2-F-5-Cl) Me O O V-144 Ph(2-F-6-Cl) Me O O V-145 Ph(3-Cl-4-F) Me O O V-146 Ph(2-Cl-3-F) Me O O V-147 Ph(2-Cl-4-F) Me O O V-148 Ph(2-Cl-5-F) Me O O V-149 Ph(3-Me-4-OMe) Me O O V-150 Ph(3-Me-5-OMe) Me O O V-151 Ph(2-Me-3-OMe) Me O O V-152 Ph(2-Me-4-OMe) Me O O V-153 Ph(2-Me-5-OMe) Me O O V-154 Ph(2-Me-6-OMe) Me O O V-155 Ph(3-OMe-4-Me) Me O O V-156 Ph(2-OMe-3-Me) Me O O

TABLE 60 Compound No. R¹ R² Y Z V-157 Ph(2-OMe-4-Me) Me O O V-158 Ph(2-OMe-5-Me) Me O O V-159 Ph(3-CN-4-OMe) Me O O V-160 Ph(3-OMe-4-CN) .Me O O V-161 Ph(3-Me-4-CN) Me O O V-162 Ph(3-CN-4-Me) Me O O V-163 Ph(3-NO₂-4-OMe) Me O O V-164 Ph(3-OMe-4-NO₂) Me O O V-165 Ph(3-Me-4-NO₂) Me O O V-166 Ph(3-NO₂-4-Me) Me O O V-167 Ph(3,5-F₂-4-OMe) Me O O V-168 Ph(3,5-F₂-4-Me) Me O O V-169 Ph(3,4,5-(OMe)₃) Me O O V-170

Me O O V-171

Me O O V-172

Me O O V-173

Me O O V-174

Me O O V-175

Me O O V-176

Me O O V-177

Me O O V-178

Me O O

TABLE 61 Compound No. R¹ R² Y Z V-179

Me O O V-180

Me O O V-181

Me O O V-182

Me O O V-183

Me O O V-184

Me O O V-185

Me O O V-186

Me O O V-187

Me O O V-188

Me O O V-189

Me O O V-190

Me O O V-191

Me O O V-192

Me O O

TABLE 62 Compound No. R¹ R² Y Z V-193

Me O O V-194

Me O O V-195

Me O O V-196

Me O O V-197

Me O O V-198

Me O O V-199

Me O O V-200

Me O O V-201

Me O O V-202

Me O O V-203

Me O O V-204

Me O O V-205 CH₂Ph Me O O V-206 CH₂CH₂Ph Me O O V-207 CH₂CH₂CH₂Ph Me O O V-208 CH₂CH═CHPh Me O O V-209 CH₂C≡CPh Me O O V-210 CH₂CH═NOMe Me O O

TABLE 63 Compound No. R¹ R² Y Z V-211 CH₂CH═NOEt Me O O V-212 CH₂CH═NOPr-n Me O O V-213 CH₂CH═NOPh Me O O V-214 CH₂CH(OMe)₂ Me O O V-215 CH₂CHO Me O O V-216 NH₂ Me O O V-217 NHMe Me O O V-218 NHEt Me O O V-219 NHPr-n Me O O V-220 NHPr-i Me O O V-221 NHBu-n Me O O V-222 NHBu-i Me O O V-223 NHBu-s Me O O V-224 NHCH₂Pr-c Me O O V-225 NHPen-n Me O O V-226 NHHex-n Me O O V-227 NHCH₂CH₂CH₂Cl Me O O V-228 NHCH₂CH₂CH₂F Me O O V-229 NHCH₂CH₂OMe Me O O V-230 NMe₂ Me O O V-231 NEt₂ Me O O V-232 N(Pr-n)₂ Me O O V-233 N(Bu-n)₂ Me O O V-234 N(Me)Et Me O O V-235 N(Me)CH₂CH₂OMe Me O O V-236 NHPh Me O O V-237 NHCH₂Ph Me O O V-238 N═CMe₂ Me O O V-239 N═CEt₂ Me O O V-240 N═CHNMe₂ Me O O V-241 NHC(═O)Me Me O O V-242 N[C(═O)Me]₂ Me O O V-243 NHC(═O)OMe Me O O V-244 N[C(═O)OMe]₂ Me O O V-245 NHSO₂Me Me O O V-246 NHSO₂Ph Me O O V-247 NHSO₂CH₂Ph Me O O V-248 OMe Me O O V-249 OEt Me O O V-250 OPr-n Me O O V-251 OPr-i Me O O V-252 OCH₂Pr-c Me O O V-253 OCH₂Cl Me O O V-254 OCHCl₂ Me O O

TABLE 64 Compound No. R¹ R² Y Z V-255 OCCl₃ Me O O V-256 OCH₂F Me O O V-257 OCHF₂ Me O O V-258 OCF₃ Me O O V-259 Ph Et O O V-260 Ph Pr-i O O V-261 Ph CHF₂ O O V-262 Ph Ph O O V-263 Ph Me O S V-264 Ph Me S S V-265 Me Me O S V-266 Me Me S S V-267 Ph Me O O V-268 Ph(4-OEt) Me O O V-269 Ph(2-Ph) Me O O V-270 Ph(3-Ph) Me O O V-271 Ph(4-Ph) Me O O V-272

Me O O V-273

Me O O V-274 Me

O O V-275 Et

O O V-276

Me O O V-277

Me O O V-278

Me O O V-279

Me O O

TABLE 65 Compound No. R¹ R² Y Z V-280

Me O O V-281

Me O O V-282 Ph(2-Me-4-Br) Me O O V-283 Ph(2-Me-5-I) Me O O V-284 Ph(2-Me-5-CF₃) Me O O V-285 Ph(2-Me-6-OCF₃) Me O O V-286 Ph(2-Pr-i) Me O O V-287

Me O O V-288 Ph(2-Et) Me O O V-289

Me O O V-290

Me O O V-291

Me O S V-292

Me O O V-293

Me O O V-294 CH₂COOBu-t Me O O V-295 (C₇H₁₄)CH₃ Me O O V-296 (C₉H₁₈)CH₃ Me O O V-297 Ph(2-F,4-Cl,5-OMe) Me O O V-298 Ph(2,3,4-(OMe)₃) Me O O V-299 Ph(3,5-Cl₂-4-OMe) Me O O V-300 Ph(3,5-Cl₂-4-SMe) Me O O V-301 Ph(3,5-Cl₂-4-SO₂Me) Me O O V-302 Ph(3,4,5-F₃) Me O O V-303

Me O O

TABLE 66 Compound No. R¹ R² Y Z V-304

Me O O V-305

Me O O V-306 Bu-n

O O V-307 CH₂CH(CH₃)₂

O O V-308 Ph Pen-n O O V-309 H Me O O V-310 CH₂C≡CF Me O O V-311

Me O O V-312

Me O O V-313 CH₂NH₂ Me O O V-314 CH₂NO₂ Me O O V-315 CH₂NHCH₃ Me O O V-316 CH₂N(CH₃)₂ Me O O V-317 CH₂SCH₂CF₃ Me O O V-318 CH₂SOCH₂CF₃ Me O O V-319 CH₂SO₂CH₂CF₃ Me O O V-320 CH₂OH Me O O V-321 CH₂OBn Me O O V-322 CH₂OCH₂Pr-c Me O O V-323 CH₂OPh Me O O V-324 CH₂SPh Me O O V-325 CH₂SOPh Me O O V-326 CH₂SO₂Ph Me O O V-327 CH₂CON(CH₃)₂ Me O O V-328 CH₂COCH₃ Me O O V-329 CH₂OCOCH₃ Me O O V-330 CH₂ON═CHCH₃ Me O O V-331 C₂H₄OC₂H₄SCH₃ Me O O V-332 C₂H₄OC₂H₄SOCH₃ Me O O V-333 C₂H₄OC₂H₄SO₂CH₃ Me O O

TABLE 6 Compound No. R¹ R² Y Z V-334 CH₂OCH₂CN Me O O V-335 CH₂CN Me O O V-336 OCH₂CH═CH₂ Me O O V-337 OCH₂C≡CH Me O O V-338 OPr-c Me O O V-339

Me O O V-340

Me O O V-341

Me O O V-342

Me O O V-343

Me O O V-344 Ph H O O V-346 Ph CH₂CH═CH₂ O O V-346 Ph CH₂C≡CH O O V-347 Ph Pr-c O O V-348 Ph CH₂CH═CF₂ O O V-349 Ph CH₂C≡CF O O V-350 Ph C₂H₄OCH₃ O O V-351 Ph C₂H₄OC₂H₅ O O V-352 Ph CH(Me)OEt O O V-353 Ph CH₂OPr-c O O V-354 Ph CH(OCH₃)₂ O O V-355 Ph CH₂Ph O O V-356 Ph CH═CH—Ph O O V-357 Ph C≡C—Ph O O V-358 Ph(3,4,5-Cl) Me O O V-359 N(Me)Ph Me O O V-360

Me O O V-361

Me O O V-362 CH₂CO(Bu-t) Me O O V-363 Ph(2,3,5,6-F₄) Me O O V-364 Ph[(3,5-(CF₃)₂] Me O O V-365 CH₂C(Me)═NOMe Me O O V-366 Ph(2,4,6-Me₃) Me O O V-367 Ph(2,3,4,5,6-F₅) Me O O V-368 N(Et)Ph Me O O V-369 N(Pr-i)Ph Me O O V-370 N(Me)Ph(4-F) Me O O V-371 CH₂C(Me)═NOEt Me O O

Compounds of the invention have an excellent herbicidal activity and some of them show excellent selectivity between crops and weeds and are useful as an agrochemical composition for farmland, especially as herbicides. In other words, the compounds of the invention have a herbicidal activity for various weeds during foliage treatment, soil treatment, seed dressing treatment, soil blending treatment, soil treatment before sowing, treatment at the time of sowing, soil treatment after sowing, soil covering and blending treatment at the time of sowing, and soil treatment before and after sowing for no-tillage farming of a field for cultivating agrohorticultural plants.

Hereinbelow, examples of the weeds are given, but the invention is not limited to them;

weeds of Onagraceae family: Oenothera erythrosepala, Oenothera laciniata;

weeds of Ranunculaceae family: Ranunculus muricatus, Ranunculus sardous;

weeds of Polygonaceae family: Polygonum convolvulus, Polygonum lapathifolium, Polygonum pensylvanicum, Polygonum persicaria, Rumex crispus, Rumex obtusifolius, Poligonum cuspidatum, Polygonum pensylvanicum, Persicaria longiseta, Persicaria lapathifolia, Persicaria nepalensis;

weeds of Portulacaceae family: Portulaca oleracea;

weeds of Caryophyllaceae family: Stellaria media, Cerastium glomeratum, Stellaria alsine, Spergula arvensis, Stellaria aquatica;

weeds of Chenopodiaccae family: Chenopodium album, Kochia scoparia, Chenopodium album, Chenopodium ficifolium;

weeds of Amaranthaceac family: Amaranthus retroflexus, Amaranthus hybridus, Amaranthus palmeri, Amaranthus spinosus, Amaranthus rudis, Amaranthus albus, Amaranthus viridus, Amaranthus lividus;

weeds of Brassicaceae family: Raphanus raphanistrum, Sinapis arvensis, Capsella bursa-pastoris, Lepidium virginicum, Thlaspi arvense, Descurarinia sophia, Rorippa indica, Rorippa islandica, Sisymnrium officinale, Cardamine flexuosa, Nasturtium officinale, Draba nemorosa;

weeds of Fabaceae family: Sesbania exaltata, Cassia obtusifolia, Desmodium tortuosum, Trifolium repens, Vicia sativa, Medicago lupulina, Vicia hirsuta; Kummerowia striata, Medicago polymorpha, Vicia angustifolia, Aeschynomene indica;

weeds of Malvaceae family: Abutilon theophrasti, Sida spinosa;

weeds of Violet family: Viola arvensis, Viola tricolor;

weeds of Rubiaceac family: Galium aparine;

weeds of Convolvulaceae family: Ipomoea hederacea, Ipomoea purpurea, Ipomoea hederacca var integriuscula, Ipomoea lacunosa, Convolvulus arvensis, Ipomoea indica, Ipomoea coccinea, Ipomoea triloba;

weeds of Lamiaceae family: Lamium purpureum, Lamium amplexicaule, Stachys arvensis;

weeds of Solanaceae family: Datura stramonium, Solanum nigrum, Physalis angulata, Solanum americanum, Solanum carolinense;

weeds of Serophulariaceae family: Veronica persica, Veronica arvensis, Veronica hederaefolia;

weeds of Asteraceae family: Xanthium pensylvanicum, Helianthus annuus, Matricaria chamomilla, Matricaria perforata or inodora, Chrysanthemum segetum, Matricaria matricarioides, Ambrosia artemisiifolia, Ambrosia trifida, Erigeron canadensis, Artemisia princeps, Solidago altissima, Taraxacum officinale, Anthemis cotula, Breca setosa, Sonchus oleraceus, Helianthus tuberosus, Cirsium arvense, Bidens frondosa, Bidens pilosa, Centurea cyanus, Cirsium vulgare, Lactuca scariola, Rudbeckia hirla, Rudbeckia laciniata, Rudbeckia laciniata var. hortensis Bailey, Senecio vulgais, Silybum marianum, Sonchus asper, Sonchus arvensis, Salsola kali, Bidens flondosa, Eclipta ptostrata, Bidense tipartita, Senecio madagascariensis, Coreopsis lanceolata, Rudbeckia laciniata;

weeds of Boraginaceae family: Myosotis arvensis;

weeds of Asclepiadaceae family: Asclepias syriaca;

weeds of Euphorbiaceae family: Euphorbia helioscopia, Euphorbia maculata, Acalypha australis;

weeds of Geraniaceae family: Geranium carolinianum;

weeds of Oxalidaceae family: Oxalis corymbosa;

weeds of Cucurbitaceae family: Sicyos angulatus;

weeds of Poaceae family: Echinochloa crus-galli, Setaria viridis, Setaria faberi, Digitaria sanguinalis, Eleusine indica, Poa annua, Alopecurus myosuroides, Avena fatua, Sorghum halepense, Agropyron repens, Bromus tectorum, Cynodone dactylon, Panicum dichotomiflorum, Panicum texanum, Sorghum vulgare, Alopecurus geniculatus, Lolium multiflorum, Lolium rigidum, Setaria glauca, Beckmannia syzigachne;

weeds of Commelinaceae family: Commelina communis;

weeds of Equisetaceae family: Equisetum arvense;

weeds of Papaveraceae family: Papaver rhoeas;

weeds of Cyperaceae family: Cyperus iria, Cyperus rotundus, Cyperus esculentus.

Compounds of the invention do not exhibit any phytotoxicity which causes a problem in major crops like Zea mays, Triticum aestivum, Hordeum vulgare, Oryza sativa, Sorghum bicolor, Glycine max, Gossypium spp., Beta vulgaris, Arachis hypogaea, Helianthus annuus, Brassica napus, buck wheat, sugar cane, and tobacco, and horticultural crops like flowers and vegetables.

Further, the compounds of the invention are useful for effective elimination of various weeds which cause a trouble in no-tillage farming of soybean, corn, and wheat, and they do not exhibit any problematic phytotoxicity to crops.

According to many treatment methods like soil treatment before cultivation; soil treatment after cultivation but before or after sowing; soil treatment after harrowing but before or after sowing, or treatment before or after transplanting a seedling; treatment at the time of transplanting a seedling; desalination treatment after transplanting a seedling; and foliage treatment, the compounds of the invention can exhibit an herbicidal activity for many problematic weeds in paddy field that are described below.

Hereinbelow, examples of the weeds are given, but the invention is not limited to them:

weeds of Poaceae family: Echinochloa oryzicola; Echinochloa crus-galli, Leptochloa chinensis, Isachne gtobosa, Paspalum distichum, Leersia sayanuka, Leersia oryzoides;

weeds of Scrophulariaceae family: Lindemia procumbens, Lindemia dubia, Dopatrium junceum, Gratiolajaponica, Lindernia angustifolia, Limnophila sessiliflora;

weeds of Lythraceae family: Rotala indica, Ammannia multitlora;

weeds of Elatinacease family: Elatine triandra;

weeds of Cyperacease family: Cyperus difformis, Scirpus hotarui, Eleocharis acicularis, Cyperus serotinus, Eleocharis kuroguwai, Fimbristylis miliacea, Cyperus flaccidus, Cyperus globosus, Scirpus juncoides, Scirpus wallichii, Scirpus nipponicus, Fimbristylis autumnalis, Scirpus tabernaemontani, Scirpus juncoides Rocxb., Scirpus lineolatus Franch. et Savat., Cyperus orthostachyus Franch. et Savat., Cyperus orthostachyus Franch. et Savat., Eleocharis congesta D. Don, Scirpus planiculmis Fr. Schm.;

weeds of Pontederiacease family: Monochoria vaginalis, Monochoria korsakowii, Heteranthera limosa;

weeds of Alismatacease family: Sagittaria pygnmaea, Sagittaria trifolia, Alisma canaliculatum, Sagittaria aginashi;

weeds of Potamogetonacease family: Potamogeton distinctus;

weeds of Eruocaulacease family: Eriocaulon cinercum;

weeds of Apiacease family: Oenanthe javanica;

weeds of Asteracease family: Eclipta prostrata, Bidens tripartita;

weeds of Commelinacease family: Murdannia keisak;

weeds of Characease family: Chara braunii;

weeds of Lermnacease family: Spirodela polyrhiza;

Hepaticae: Ricciocarpus natans;

Zygnemataccac: Spirogyra arcla.

Further, the compounds of the invention show no phytoxicity to paddy rice according to any cultivation method including direct sowing or transplanting of paddy rice followed by cultivation.

Further, the compounds of the invention can be used for controlling a wide spectrum of weeds thriving in a lot for industrial facilities like a slope of a levee, a riverbed, a shoulder and a slope of a road, a railway site, park spaces, grand, a parking lot an airport, a factory and a storage facility, a non-crop land like fallow fields, and vacant lots in city, which needs the weed control, or an orchard, a pasture land, a grass land, a forest land, etc.

Moreover, according to foliage treatment, water-surface application, etc., the compounds of the invention can exhibit a herbicidal activity for water weeds which occur in river, waterway, canal, reservoir, etc., wherein the water weeds include Pontederiaceae family: Eichhornia crassipes; Salvinia natans family: Azolla imbricata, Azolla japonica. Salvinia natanas; Araceaei family: Pistia stratiotes; Haloragaceae family: Myriophyllum brasilensa, Myriophyllum verticillatum; Myriophyllum spicatum; Myriophyllum matogrossense; Azollaceae family: Azolla cristata; Scrophulariaccase family: Veronica anagallis-aquatica; Amaranthaceae family: Alternanthera philoxeroides; Gymnocoronis spilanthoides; Poaceate family: Spartina anglica; Apiaceae family: Hydrocotyle ranunculoides; Hydrocharitaceae family: Hydrilla verticillata, Egeria densa; Cabpmbaceae family: Cabomba caroliniana; and Lemnaceae family: Wolffia globosa.

The agrohorticultural plants described in the invention include crops like corn, rice, wheat, barley, rye, sorghum, cotton, soybean, peanuts, buck wheat, sugar beet, rapeseed, sun flower, sugar cane, and tobacco; vegetable like vegetables of Solanaceae (eggplant, tomato, bell pepper, pepper, potato, etc.), vegetables of Cucurbitaceae (cucumber, pumpkin, zucchini, water melon, melon, etc.), vegetables of Cruciferae (daikon, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), vegetables of Compositae (burdock, crown daisy, artichoke, lettuce, etc.), vegetables of Liliaceae (scallion, onion, garlic, asparagus, etc.), vegetables of Apiaccae (carrot, parsley, celery, parsnip, etc.), vegetables of Chenopodiaceae (spinach, leaf beet, etc.), vegetables of Lamiaccae (beefsteak plant, mint, basil, etc.), vegetables like strawberry, sweet potato, yam, and taro; kernel fruits (apple, western pear, Japanese pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, Japanese apricot, cherry, apricot, prune, etc.), mandarins (tangerine, orange, lemon, lime, grape fruits, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashewnut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), fruits like grape, persimmon, olive, loquat, banana, coffee, date, coconut, and oil nut; trees other than fruit tree like tea, mulberry, roadside trees (ash tree, birch, American flowering dogwood, eucalyptus, gingko, lilac, maple tree, oak tree, poplar tree, redbud tree, liquidambar, sycamore, zelkova, Japanese arborvitae, Japanese fir, hemlock spruce, juniper, pine tree, spruce, yew, elm, a horse chestnut, etc.), coral, Buddist pine, cedar, Japanese cypress, croton, spindle tree, Photinia glabra, etc.; grasses like turf (turf, gold turf, etc.), Bermuda grasses (Cynodon dactylon, etc.), bentgrasses (creeping bentgrass, Agrostis alba L., Agrostis capillaries, etc.), bluegrasses (Kentucky bluegrass, Poa trivialis L., etc.), fcscues (tall fescue, chewings fescue, Festuca rabra L., etc.), rye grasses (Lolium temulentum L., Lolium perenne L., etc.), orchard grass, timothy, etc.; oil crops like oil coconut, Jatropha curcas, etc.; flowers (rose, carnation, mum, prairie gentian, common gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, Chinese aster, Gentiana scabra var. buergeri, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, cauliflower, primula, poincetia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia, etc.); a foliage plant, etc., but the invention is not limited thereto.

The agrohorticultural plant described in the invention includes a plant given with resistance to HPPD inhibitor like Isoxaflutole, ALS inhibitor like Imazetaphyr and tifensulfuron methyl, EPSP synthase inhibitor like glifosate, glutamine synthase inhibitor like glufosinate, acetyl CoA carboxylase inhibitor like sethoxydim, PPO inhibitor like flumioxazin, and herbicides like bromoxinil, dicamba and 2,4-D according to classic breeding method or genetic recombination method.

Examples of the “agrohorticultural plant” given with resistance according to classic breeding include rapeseed, wheat, sun flower, rice, and corn that are resistant to imidazolinone-based ALS inhibitor like Imazetaphyr, and they are already commercially available in the name of Clearfield <trade name>.

Similarly, there is soybean resistant to sulfonylurea-based ALS inhibitor like tifensulfuron metil as produced by classic breeding method, and it is already commercially available in the trade name of STS Soybean. Similarly, examples of the “agrohorticultural plant” given with resistance to an acetyl CoA carboxylase inhibitor like trione-oxime based or aryloxyphenoxy propionic acid-based herbicides according to classic breeding include SR Corn. The horticultural plant given with resistance to acetyl CoA carboxylase is described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), Vol 87, pages 7175 to 7179 (1990), etc. Further, a mutant acetyl CoA carboxylase which is resistant to acetyl CoA carboxylase inhibitor is reported in Weed Science Vol. 53, pages 728 to 746 (2005), and by introducing a mutant gene of acetyl CoA carboxylase to a plant by genetic recombination technique or by introducing mutation for giving resistance to acetyl CoA carboxylase of crops, a plant which is resistant to an acetyl CoA carboxylase inhibitor can be produced. Further, by having site-specific amino acid substitution mutation on a gene of crops based on introduction of a nucleic acid with base substitution mutation to a plant cell as represented by chimeraplasty technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318), a plant which is resistant to acetyl CoA carboxylase inhibitor/herbicides can be produced.

Examples of the “agrohorticultural plant” given with resistance according to genetic recombination technique include corn, soybean, cotton, rapeseed, and sugar beet that are resistant to glyfosate, and they are already commercially available in the name of RoundupReady <trade name>, AgrisureGT, etc. Similarly, there are corn, soybean, cotton, and rapeseed varieties that are produced to be resistant to glufosinate by genetic recombination technique, and they are already commercially available in the name of LibertyLink <trade name>, etc. Similarly, cotton having resistance to bromoxinil is also made available by genetic recombination technique and is already commercially available in the trade name of BXN.

The “agrohorticultural plant” includes a plant which is engineered by genetic recombination technique to synthesize a selective toxin like Bacillus spp., for example.

Examples of the insecticidal toxin expressed in a genetically engineered plant include an insecticidal protein originating from Bacillus cereus or Bacillus popilliae; 5-endotoxin originating from Bacillus thuringiensis like Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, and Cry9C, and insecticidal proteins like VIP1, VIP2, VIP3, and VIP3A; insecticidal proteins originating from a nematode; animal-produced toxins like scorpion toxin, spider toxin, bee toxin, and insect specific neurotoxin; filamentous fungus toxin; plant lectin; agglutinin; protease like trypsin inhibitor, serine protease, patatin, cistatin, and papain inhibitor; ribosome inactivating proteins (RIP) like lysine, corn-RIP, abrin, saporin, and briodin; enzymes for steroid metabolism like 3-hydroxysteroid oxidase, ecdisteroid-UDP-glycosyl transferase, and cholesterol oxidase; cedysone inhibitor; HMG-CoA reductase; ion channel inhibitors like sodium channel inhibitor and potassium channel inhibitor; juvenile hormone esterase; natriuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glucanase.

Examples of the toxins expressed in a genetically engineered plant include a hybrid toxin, a partially deleted toxin, and a modified toxin of an insecticidal protein like 8-endotoxin including Cry1Ab, Cry1Ac, Cry1F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1, and Cry9C, and insecticidal proteins including VIP1, VIP2, VIP3, and VIP3A. The hybrid toxin is produced by new combination of domains having different proteins based on recombination technique. Examples of the partially deleted toxin include Cry1Ab in which part of amino acid sequence is deleted. In the modified toxin, one or more amino acids of a natural type toxin are replaced with other amino acids.

Examples of the toxins and recombinant plants capable of producing the toxins are described in EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878, and WO03/052073, and the like.

The toxins contained in such recombinant plant can provide a plant with a resistance to harmful insects of Coleoptera, harmful insects of Diptera, and harmful insects of Lepidoptera.

A genetically engineered plant which contains one or more pesticidal harmful insect-resistant gene and expresses one or more toxins is known, and some are already commercially available. Examples of the genetically engineered plant include YieldGard <trade name> (corn variety which expresses Cry1Ab toxin), YieldGard Rootworm <trade name> (corn variety which expresses Cry3Bb1 toxin), YieldGard Plus <trade name> (corn variety which expresses Cry1Ab and Cry3Bb1 toxin), Herculex I <trade name> (corn variety which expresses phosphinotricine N-acetyl transferase (PAT) to give resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B <trade name> (cotton variety which expresses Cry1Ac toxin), Bollgard I <trade name> (cotton variety which expresses Cry1Ac toxin), Bollgard II <trade name> (cotton variety which expresses Cry1Ac and Cry2Ab toxin), VIPCOT <trade name> (cotton variety which expresses VIP toxin), NewLeaf <trade name> (potato variety which expresses Cry3A toxin), NatureGard <trade name> Agrisure <trade name> GTAdvantage (GA21 glyfosate resistant trait), Agrisure <trade name> CB Advantage (Bt11 Corn Borer (CB) trait), and Protecta <trade name>.

The “agrohorticultural plant” includes a plant which is genetically engineered to have an ability of producing an anti-pathogenic substance having selective activity.

Examples of the anti-pathogenic substance include PR proteins (PRPs, described in EP-A-0392225); ion channel inhibitors like sodium channel inhibitor and calcium channel inhibitor (KP1, KP4, KP6 toxin that are produced by virus are known); stilbene synthase; bibenzyl synthase; chitinase; glucanase; and a substance produced by a microorganism like peptide antibiotics, antibiotics having heterocycle, and a protein factor related to resistance to plant disease (referred to as “plant disease resistant gene”, and described in WO03/000906).

Such anti-pathogenic substances and plants genetically engineered to produce the substances are described in EP-A-0392225, WO95/33818, and EP-A-0353191, etc.

The “agrohorticultural plant” includes a plant which is given with useful traits like a trait of having modified oil components or a trait for producing enhanced amount of amino acid according to genetic recombination technique. Examples thereof include VISTIVE <trade name> (low-linolenic soybean having reduced linolen content) or high-lysine (high oil) corn (corn having enhanced amount of lysine or oil).

Further, there is also a stack variety in which multiple traits of classic herbicidal trait or herbicides-resistant gene, pesticidal insect-resistant gene, anti-pathogenic substance-producing gene, and useful traits like a trait of having modified oil components or a trait for producing enhanced amount of amino acid are combined.

The agrochemical composition of the invention contains the triazine derivative of the invention or a salt thereof, and an agriculturally acceptable carrier. The agrochemical composition of the invention may contain additive components that may be normally employed for agrochemical formulations, as needed.

Examples of the additive components include carriers such as solid carrier and liquid carrier, surface active agent, binder, tackifier, thickener, coloring agent, spreader, sticker, antifreezing agent, anticaking agent, collapsing agent, decomposition inhibitor and the like.

If necessary, an antiseptic agent, a piece of plant (soybean powder, tobacco powder, walnut powder, wheat powder, wood powder, hulls, wheat hulls, outer hulls, sawdust, pulp flock, corn stalk, nut shell, fruit core chips, etc.) and the like may also be employed as additive components.

These additive components may be used alone or in combination of two or more kinds.

The above additive components will be described.

Examples of the solid carrier include natural minerals such as quartz, clay, kaolinite, pyrophillite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomite; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; organic solid carriers such as synthetic silicic acid, synthetic silicate, starch, cellulose and plant powder; plastic carriers such as polyethylene, polypropylene and polyvinylidene chloride; and the like. These may be used alone or in combination of two or more kinds.

Examples of the liquid carrier include alcohols classified broadly into monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin; polyhydric alcohol derivatives such as propylene based glycol ether; ketones such as acetone, methylethyl ketone, methylisobutyl ketone, diisobutyl ketone, and cyclohexanone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as n-paraffin, naphthene, isoparaffin, kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate and dimethyl adipate; lactones such as γ-butyrolactone; amides such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide and N-alkyl pyrrolidinone; nitriles such as acetonitrile; sulfur compounds such as dimethylsulfoxide; vegetable oils such as soybean oil, canola oil, cottonseed oil and castor oil; water; and the like. These may be use alone or in combination of two or more kinds.

The surface active agent is not particularly limited, but preferred are those either turning into a gel in water or exhibiting swelling property. Examples thereof include non-ionic surface active agents such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formaldehyde condensate, polyoxyethylene polyoxypropylene block polymer, alkylpolyoxyethylene polypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether silicone, ester silicone, fluorine-based surface active agent, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil; anionic surface active agents such as alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate, alkyl benzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, naphthalenesulfonic acid formaldehyde condensate salt, alkylnaphthalenesulfonic acid formaldehyde condensate salt, fatty acid salt, polycarboxylate, N-methyl-fatty acid sarcosinate, resin acid salt, polyoxyethylene alkyl ether phosphate, and polyoxyethylene alkylphenyl ether phosphate; cationic surface active agents such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, and alkyldimethylbenzalkonium chloride; amino acid or betaine type amphoteric surface active agents; and the like.

These surface active agents may be used alone or in combination of two or more kinds.

Examples of the binder or tackifier include carboxymethyl cellulose and a salt thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol having an average molecular weight of 6,000 to 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000 natural phospholipids (for instance, cephalic acid, lecithin) and the like.

Examples of the thickener include water-soluble polymers such as xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxy vinyl polymer, acrylic polymer, starch derivative and polysaccharide; fine inorganic powders such as high purity bentonite and white carbon; and the like.

Examples of the coloring agent include inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dye, azo dye and metal phthalocyanine dye; and the like.

Examples of the extender agent include silicone surface active agent, cellulose powder, dextrin, processed starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, maleic acid-styrenes-methacrylic acid copolymer, half ester of polyhydric alcohol polymer with dicarboxylic anhydride, water-soluble salt of polystyrene sulfonate and the like.

Examples of the spreader include various surface active agents such as dialkyl sodium sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether and polyoxyethylene fatty acid ester, paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinylalkyl ether, alkylphenol-formaldehyde condensate, synthetic resin emulsion and the like.

Examples of the antifreezing agent include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, glycerin, and the like.

Examples of the anticaking agent include polysaccharides such as starch, alginic acid, mannose and galactose, polyvinylpyrrolidone, white carbon, ester gum, petroleum resin and the like.

Examples of the collapsing agent include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic chelate compound, sulfonated styrene-isobutylene-maleic anhydride copolymer, starch-polyacrylonitrile graft copolymer and the like.

Examples of the decomposition inhibitor include desiccants such as zeolite, quicklime and magnesium oxide; antioxidants that are based on phenol, amine, sulfur and phosphoric acid; ultraviolet absorbers that are based on salicylic acid, benzophenone or the like; and the like.

Examples of the antiseptic agent include potassium sorbate, 1,2-benzthiazolin-3-one and the like.

According to the agrochemical composition of the invention, in the case where the additive components described above are included, the content ratio of the carrier (weight base) is generally selected from 5 to 95%, preferably from 20 to 90%, the content ratio of the surface active agent is generally selected from 0.1 to 30%, preferably from 0.5 to 10%, and the content ratio of other additives are selected from 0.1 to 30%, preferably from 0.5 to 10%.

The agrochemical composition of the invention can be used in any forms such as liquid formulation, emulsifiable concentrate, wettable powder, dust, oil solution, water dispersible granule, flowable, granule, Jumbo formulation, and suspoemulsion,

On the occasion of use, the agrochemical composition can be sprayed after being diluted in an adequate concentration or be used directly.

The agrochemical composition of the invention can be used for foliage application, soil application, water-surface application or the like. The agrochemical composition of the invention, in particular the herbicides, is used for soils, i.e., farmland of fields and paddy fields in which agrohorticultural plants are cultivated.

For the agrochemical composition of the invention, the blending ratio of active component according to the invention is arbitrarily selected as needed. In the case of dust, granule or the like, the ratio should be arbitrarily selected from 0.01 to 10% (by weight), preferably from 0.05 to 5% (by weight). In the case of emulsifiable concentrate, wettable powder or the like, the ratio should be arbitrarily selected from 1 to 50% (by weight), preferably from 5 to 30% (by weight). In addition, in the case of a flowable agent or the like, the ratio should be arbitrarily selected from 1 to 40% (by weight), preferably from 5 to 30% (by weight).

The application amount of the agrochemical composition according to the invention varies depending on a kind of a compound to be used, target weed, growth pattern, environmental conditions, formulation for use or the like. In the case of a direct use of dust, granule or the like, the amount should be arbitrarily selected from 1 g to 50 kg, preferably from 10 g to 10 kg per hectare as an active component. Further, in the case of using in a liquid form, for example, in the case of emulsifiable concentrate, wettable powder, flowable agent or the like, the amount should be arbitrarily selected from 0.1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

The agrochemical composition of the invention has an excellent herbicidal activity, and therefore is useful as herbicides in particular.

According to purpose of use, the agrochemical composition of the invention may be formulated, mixed or used in combination with at least one additional agrochemically active component, for example, a plant disease control component, a pesticidal component, an acaricidal component, an nematocidal component, a synergistic agent component, an attracting component, a repellent component, a herbicidal component, a safener component, a microbial pesticidal component, a plant growth control component, a fertilizer component, a soil improving agent, etc.

When the composition is used in combination with other agrochemically active component or fertilizer, the preparation of each individual component may be mixed with others at the time of use. Further, each preparation of an individual component may be used in order, or used with an interval of some days. When the preparations are used with an interval of some days, they may be applied with an interval of 1 day to 40 days, for example, although it may vary depending on each component to be used.

According to the agrochemical composition of the invention, when a mixture of at least one compound selected from the triazine derivatives represented by Formula 1 and their salt and at least one kind selected from other agrochemically active components is used, they are generally used in weight ratio of 100:1 to 1:100, preferably 20:1 to 1:20, and particularly 10:1 to 1:10.

Among other agrochemically active components that may be mixed or used in combination with the compound of the invention in the agrochemical composition of the invention, examples of known herbicides or plant growth control agents are described below, but the invention is not limited thereto.

[Herbicides]

A1. Acetyl CoA Carboxylase (ACCase) Inhibition Type Herbicides

(A1-1) Aryl oxy phenoxy propionic acid-based compound: clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, diclofop-P-methy), fenoxaprop-P-ethyl, fluazifop-butyl, fluazifop-P-butyl, haloxyfop, haloxyfop-etotyl, haloxyfop-P, metamifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, and fenthiaprop-ethyl

(A1-2) Cyclohexane dione-based compound: alloxydim, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim

(A1-3) Phenyl pyrazoline-based compound: aminopyralid, and pinoxaden

B. Acetolactate Synthase (ALS) Inhibition Type Herbicides

(B-1) Imidazolinone-based compound: imazamethabenz-methyl, imazamox, imazapic (including salts with amine or the like), imazapyr (including salts with isopropylamine or the like), imazaquin, and imazetbapyr

(B-2) Pyrimidinyloxy benzoic acid-based compound: bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, and pyrimisulfan

(B-3) Sulfonylamino carbonyl triazolinone-based compound: flucarbazone-sodium, thiencarbazone (including sodium salt, methyl ester, or the like), propoxycarbazone-sodium, procarbazone-sodium

(B-4) Sulfonylurea-based compound: amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl-sodium, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron-sodium, triflusulfuron-methyl, tritosulfuron, orthosulfamuron, propyrisulfuron, metazosulfuron, and flucetosulfuron

(B-5) Triazolopyrimidine-based compound: cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyroxsulam, and HNPC-C-9908 (code number)

C1. Herbicides 1 for Photosystem II Photosynthesis Inhibition

(C1-1) Phenylcarbamate-based compound: desmedipham and phenmedipham

(C1-2) Pyridazinone-based compound: chloridazon and brompyrazon

(C1-3) Triazine-based compound: ametryn, atrazine, cyanazine, desmetryne, dimethametryn, eglinazine-ethyl, prometon, prometryn, propazine, simazine, simetryn, terbumecton, terbuthylazine, terbutryn, and trietazine

(C1-4) Triazinone-based compound: metamitron and metribuzin

(C1-5) Triazolinone-based compound: amicarbazone

(C1-6) Uracil-based compound: bromacil, lenacil, and terbacil

C2. Herbicides 2 for Photosystem II Photosynthesis Inhibition

(C2-1) Amide-based compound: pentanochlor and propanil

(C2-2) Urea-based compound: chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, linuron, methabenzthiazuron, methobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and metobenzuron

C3. Herbicides 3 for Photosystem II Photosynthesis Inhibition

(C3-1) Benzothiadiazone-based compound: bentazone

(C3-2) Nitrile-based compound: bromofenoxim, bromoxynil (including ester form with butyric acid, octanoic acid and heptanoic acid), and ioxynil

(C3-3) Phenyl pyrazine-based herbicide compound: pyridafol, and pyridate

D. Photosystem I Radical Generation Type Herbicides

(D-1) Bipyridinium-based compound: diquat and paraquat dichloride

E. Protoporpyrinogen Oxidase (PPO) Inhibition Herbicides

(E-1) Diphenyl ether-based compound: acifluorfen-sodium, bifenox, chlomethoxyfen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fomesafen, lactofen, and oxyfluorfen

(E-2) N-Phenylphthalimide-based compound: cinidon-ethyl, flumiclorac-pentyl, flumioxazin, and chlorphthalim

(E-3) Oxy diazole-based compound: oxadiargyl and oxadiazon

(E-4) Oxazolidinedione-based compound: pentoxazone

(E-5) Phenylpyrazole-based compound: fluazolate and pyraflufen-ethyl

(E-6) Pyrimidinedione-based compound: benzfendizone, butafenacil, and saflufenacil

(E-7) Thiadiazole-based compound: fluthiacet-methyl and thidiazimin

(E-8) Triazolinone-based compound: azafenidin, carfentrazone-ethyl, sulfentrazone, and bencarbazone

(E-9) Other compounds: flufenpyr-ethyl, profluazol, pyraclonil, SYP-298 (code number), and SYP-300 (code number)

F1. Phytoene Desaturase (PDS) Inhibition Herbicides

(F1-1) Pyridazinone-based compound: norflurazon

(F1-2) Pyrimidine carboxamide-based compound: diflufenican and picolinafen

(F1-3) Other compounds: beflubutamid, fluridone, fluorochloridone, and flurtamone

F2. 4-Hydroxyphenylpyruvate Deoxygenase (HPPD) Inhibition Herbicides

(F2-1) Callistemon-based compound: mesotrione

(F2-2) Isoxazole-based compound: pyrasulfotole, isoxaflutole, and isoxachlortole

(F2-3) Pyrazole-based compound: benzofenap, pyrazolynate, and pyrazoxyfen

(F2-4) Triketone-based compound: sulcotrione, tefuryltrion, tembotrione, pyrasulfotole, topramezone, bicyclopyrone, and 4-chloro-5-(1,3-dioxocyclohexa-2-yl) carbonyl-2,3-dihydrobenzothiophene-1,1-dioxide

F3. Carotenoid Biosynthesis Inhibition (Unknown Target) Herbicides

(F3-1) Diphenyl ether-based compound: aclonifen

(F3-2) Isoxazotidinone-based compound: clomazone

(F3-3) Triazole-based compound: amitrole

G EPSP Synthase Synthesis Inhibition (Aromatic Amino Acid Biosynthesis Inhibition) Type Herbicides

(G-1) Glycine-based compound: glyphosate (including salts with sodium, amine, propylamine, isopropylamine, dimethylamine, and trimesium)

H. Glutamine Synthesis Inhibition Herbicides

(H-1) Phosphinic acid-based compound: bilanafos, glufosinate (including salts with amine or sodium)

I. Dihydropteroic Acid (DHP) Inhibition Herbicides

(I-1) Carbamate-based compound: asulam

K1. Microtubule Association Inhibition Type Herbicides

(K1-1) Benzamide-based compound: propyzamide and tebulam

(K1-2) Benzoic acid-based compound: chlorothal-dimethyl

(K1-3) Dinitroaniline-based compound: benfluralin, butralin, dinitramine, ethalfluralin, fluchlomlin, oryzalin, pendimethalin, prodiamine, and trifluralin

(K1-4) Phosphoroamidate-based compound: amiprofos-methyl and butamifos

(K1-5) Pyridine-based compound: dithiopyr and thiazopyr

K2. Mitosis/Microtubule Tissue Formation Inhibition Herbicides

(K2-1) Carbamate-based compound: carbetamide, chlorpropham, propham, swep, and karbutilate

K3. Very Long-Chain Fatty Acid (VLCFA) Synthase Inhibition Herbicides

(K3-1) Acetamide-based compound: diphenamid, napropamide, and naproanilide

(K3-2) Chloroacetamide-based compound: acetochlor, alachlor, butachlor, butenachlor, diethatyl-ethyl, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, pethoxamid, pretilachlor, propachlor, propisochlor, S-metolachlor, and thenylchlor

(K3-3) Oxyacetamide-based compound: flufenacet and mefenacet

(K3-4) Tetrazolinone-based compound: fentrazamide

(K3-5) Other compounds: anilofos, bromobutide, cafenstrole, indanofan, piperophos, fenoxasulfone, pyroxasulfone, and ipfencarbazone

L. Cellulose Synthesis Inhibition Herbicides

(L-1) Benzamide-based compound: isoxaben

(L-2) Nitrile-based compound: dichlobenil, chlorthiamid

(L-3) Triazolecarboxamide-based compound: flupoxame

M. Uncoupler (Cell Membrane Distruction) Type Herbicides

(M-1) Dinitrophenol-based compound: dinoterb and DNOC (including salts with amine or sodium)

N. Lipid Bioxynthesis (Excluding ACCase Inhibition) Inhibition Herbicides

(N-1) Benzofuran-based compound: benfuresate and ethofumesate

(N-2) Halogenated carboxylic acid-based compound: dalapon, flupropanate, and TCA (including salts with sodium, potassium, or ammonia)

(N-3) Phosphorodithioate-based compound: bensulide

(N-4) Thiocarbamate-based compound: butylate, cycloate, dimepiperate, EPTC, esprocarb, molinate, orbencarb, pebulate, prosulfocarb, thiobencarb, tiocarbazil, tri-allate, and vernolate

O. Auxin Synthesis Inhibition Herbicides

(O-1) Benzoic acid-based compound: chloramben, 2,3,6-TBA, and dicamba (including salts with amine, diethyl amine, triethanolamine, isopropylamine, sodium, or lithium)

(O-2) Phenoxy carboxylic acid-based compound: 2,4,5-T, 2,4-D (including salts with amine, diethyl amine, isopropylamine, diglycolamine, sodium, or lithium), 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, MCPA, MCPA-thioethyl, MCPB (including sodium salt and ethyl ester), mecoprop (including salts with sodium, potassium, isopropylamine, triethanol amine, and dimethylamine), and mecoprop-P

(O-3) Pyridine carboxylic acid-based compound: clopyralid, fluroxypyr, picloram, triclopyr, and triclopyr-butotyl

(O-4) Quinoline carboxylic acid-based compound: quinclorac and quinmerac

(O-5) Other compounds: benazolin

P. Auxin Transport Inhibition Type Herbicides

(P-1) Phthalamates-based compound: naptalam (including salts with sodium)

(P-2) Semicarbazone-based compound: diflufenzopyr

Z. Herbicides with Unknown Mode of Action

Flamprop-M (including methyl, ethyl, and isopropyl ester), flamprop (including methyl, ethyl, and isopropyl ester), chloroflurenol-methyl, cinmethylin, cumyluron, daimuron, methyldymuron, difenzoquat, etobenzanid, fosamine, pyributicarb, oxaziclomefone, acrolein, AE-F-150944 (code number), aminocyclopyrachlor, cyanamide, heptamaloxyloglucan, indaziflam, triaziflam, quinoclamine, endothal-disodium, phenisopham, BDPT, BAU-9403 (code number), SYN-523 (code number, SYP-249 (code number), JS-913 (code number), IR-6396 (code number), metiozolin, Triafamone, HW-02 (code number), and BCS-AA10579 (code number)

[Plant Growth Controlling Compounds]

1-Methylcyclopropene, 1-naphthylacetamide, 2,6-diisopropylnaphthalene, 4-CPA, benzylaminopurine, ancymidol, aviglycine, carvone, chlormequat, cloprop, cloxyfonac, cloxyfonac-potassium, cyclanilide, cytokinins, daminodide, dikegulac, dimethipin, ethephon, ethychlozate, flumetralin, flurenol, flurprimidol, forchlorfenuron, gibberellin acid, inabenfide, indol acetic acid, indol butyric acid, maleic hydrazide, mefluidide, mepiquat chloride, n-decanol, paclobutrazol, prohexadione-calcium, prohydrojasmon, sintofen, thidiazuron, triacontanol, trinexapac-ethyl, uniconazole, uniconazole-P, and ecolyst

Hereinbelow, known safeners which may be mixed or used in combination with the compound of the invention are exemplified, but the invention is not limited thereto: benoxacor, furilazole, dichlormid, dicyclonone, DKA-24 (N1,N2-diallyl-N2-dichloroacctylglycinamide), AD-67 (4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane), PPG-1292 (2,2-dichloro-N-(1,3-dioxan-2-yl methyl)-N-(2-propenyl)acetamunide), R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine), cloquintcet-mexyl, naphthalic anhydride (1,8-naphthalic anhydride), mefenpyr-diethyl, mefenpyr, mefenpyr-ethyl, fenchlorazole O ethyl, fenclorim, MG-191 (2-dichloromethyl-2-methyl-1,3-dioxane), cyometrinil, flurazole, fluxofenim, isoxadifen, isoxadifen-ethyl, mecoprop, MCPA, daimuron, 2,4-D, MON4660 (code number), oxabetrinil, cyprosulfamide, lower alkyl substituted benzoic acid, and TI-35 (code number).

Among other herbicidically active components that may be mixed or used in combination with the compound of the invention, known plant disease control agents are described below, but the invention is not limited thereto.

1. Nucleic Acid Biosynthesis Inhibitor

acyl alanine compound: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, and metalaxyl-M;

oxazolidinone-based compound: oxadixyl;

butylol lactone-based compound: clozylacon and ofurace;

hydroxy-(2-amino)pyrimidine-based compound: bupirimate, dimethirimol, and ethirimol;

isoxazole-based compound: hymexazol;

isothiazolone-based compound: octhilinone;

carboxylic acid-based compound: oxolinic acid

2. Mitosis and Cell Differentiation Inhibitor

benzimidazole-based compound: benomyl, carbendazim, fuberidazole, and thiabendazole;

thiophanate-based compound: thiophanate and thiophanate-methyl;

N-phenylcarbamate-based compound: diethofencarb;

toluamide-based compound: zoxamide;

phenylurea-based compound: pencycuron;

pyridinylmethyl benzamide-based compound: fluopicolide

3. Respiration Inhibitor

pyrimidine amine-based compound: diflumetorim;

carboxamide-based compound: benodanil, flutolanil, mepronil, fluopyram, fenfuram, carboxin, oxycarboxin, thifluzamide, bixafen, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, and boscalid;

methoxy acrylate-based compound: azoxystrobin, enestroburin, picoxystrobin, and pyraoxystrobin;

methoxycarbamate-based compound: pyraclostrobin, pyrametostrobin;

oxyiminoacetate compound: kresoxim-methyl and trifloxystrobin;

oxyiminoacetamide-based compound: dimoxystrobin, metominostrobin, and orysastrobin;

oxazolidinedione-based compound: famoxadone;

dihydrodioxadine-based compound; fluoxastrobin;

imidazolinone-based compound: fenamidone;

benzylcarbamate-based compound: pyribencarb;

cyanoimidazole-based compound: cyazofamid;

sulfamoyltriazole-based compound: amisulbrom;

dinitrophenylcrotonic acid-based compound: binapacryl, meptyldinocap, and dinocap;

2,6-dinitroaniline-based compound: fluazinam;

pyrimidinone hydrazone-based compound: ferimzone;

triphenyl tin-based compound: TPTA, TPTC, TPTH;

thiophenecarboxamide-based compound: silthiofam;

triazolopyrimidyl amine-based compound: ametoctradin

4. Amino acid and protein synthesis inhibitor

anilino pyrimidine-based compound: cyprodinil, mepanipyrim, and pyrimethanil;

enopyranuronic acid-based antibiotics: blasticidin-S and mildiomycin;

hexopyranosyl-based antibiotics: kasugamycin;

glucopyranosyl-based antibiotics: streptomycin;

tetracycline-based antibiotics: oxytetracycline;

other antibiotics: gentamycin

5. Preparation Acting on Signal Transduction Pathway

quinoline-based compound: quinoxyfen;

quinazoline-based compound: proquinazid;

phenylpyrrol-based compound: fenpiclonil and fludioxonil;

dicarboximide-based compound: chlozolinate, iprodione, procyrnidone, and vinclozolin

6. Lipid and Cell Membrane Synthesis Inhibitor

phosphorothiorate-based compound: edifenphos, iprobenfos, and pyrazophos;

dithiolane-based compound: isoprothiolane;

aromatic hydrocarbon-based compound: biphenyl, chloroneb, dicloran, quintozene, tecnazene, and tolclofos-methyl;

1,2,4-thiadiazole-based compound: etridiazole;

carbamate-based compound: iodocarb, propamocarb-hydrochloride, and prothiocarb;

cinnamic amide-based compound: dimethomorph and flumorph;

valine amide carbamate-based compound: benthiavalicarb-isopropyl, iprovalicarb, and valifenalate;

mandelic amide-based compound: mandipropamid;

Bacillus subtilis and bactericidal lipopeptide product: Bacillus subtilis (strain: QST 713)

7. Sterol Biosynthesis Inhibitor

piperazine-based compound: triforine;

pyridine-based compound: pyrifenox;

pyrimidine-based compound: fenarimol and nuarimol;

imidazole-based compound: imazalil, oxpoconazole-fumarate, pefurazoate, prochloraz, and triflumizole;

triazole-based compound: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, furconazole, furconazole-cis, and quinconazole;

morpholine-based compound: aldimorph, dodemorph, fenpropimorph, and tridemorph;

piperidine-based compound: fenpropidin and piperalin;

spiroketal amine-based compound: spiroxamine;

hydroxy anilide-based compound: fenhexamid;

thiocarbamate-based compound: pyributicarb;

aryl amine-based compound: naftifine and terbinafine

8. Glucan Biosynthesis Inhibitor

glucopyranosyl-based antibiotics: validamycin;

peptidyl pyridine nucleotide compound: polyoxin

9. Melanine Synthesis Inhibitor

isobenzofuranone-based compound: phthalide;

pyrroloquinoline-based compound: pyroquilon;

triazolobenzothiazole-based compound: tricyclazole;

carboxamide-based compound: carpropamid, diclocymet;

propionamide-based compound: fenoxanil

10. Preparation for Inducing Resistance to Plant Disease

benzothiadiazole-based compound: acibenzolar-S-methyl;

benzoisothiazole-based compound: probenazole;

thiadiazole carboxamide-based compound: tiadinil and isotianil;

natural product: laminarin

11. Preparation with Unknown Mode of Action or Multiple Mode of Action

copper compound: copper hydroxide, copper dioctanoate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper, Bordeaux mixture, and copper nonyl phenol sulphonate;

sulfur compound: sulfur;

dithiocarbamate-based compound: ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram, and cufraneb;

phthalimide-based compound: captan, folpet, and captafol;

chloronitrile-based compound: chlorothalonil;

sulfamide-based compound: dichlorfluanid, tolylfluanid;

guanidine-based compound: guazatine, iminoctadine-albesilate, and iminoctadine-triacetate, dodine;

other compounds: anilazine, dithianon, cymoxanil, vfosetyl (alminium, calcium, and sodium), phosphorous acid and salts, tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, ethaboxam, cyflufenamid, metrafenone, potassium bicarbonate, sodium bicarbonate, BAF-045 (code number), BAG-010 (code number), benthiazole, bronopol, carvone, chinomethionat, dazomet, DBEDC, debacarb, dichlorophen, difenzoquat-methyl sulfate, dimethyl disulfide, diphenylamine, ethoxyquin, flumetover, fluoroimide, flutianil, fluxapyroxad, furancarboxylic acid, metam, nabam, natamycin, nitrapyrin, nitrothal-isopropyl, o-phenylphenol, oxazinylazole, oxyquinoline sulfate, phenazine oxide, polycarbamate, pyriofenone, S-2188 (code number), silver, SYP-Z-048 (code number), tebufloquin, tolnifanide, trichlamide, mineral oils, and organic oils

12. Microorganisms and Products of Microorganisms

Agrobacterium radiobacter, Fermented product from Aspergillus spp., Bacillus spp., Harpin protein, Erwinia carotovora, Fusarium oxysporum, Gliocladium spp., Laccase, Pseudomonas spp., Talaromyces spp., Trichoderma spp., Extract from mushroom, and Bacteriophage

Among other herbicidically active components that may be mixed or used in combination with the compound of the invention, known pesticides, acaricides, nematocides, and synergistic agents are described below, but the invention is not limited thereto.

[Pesticides, Acaricids & Nematocides]

1. Acetylcholine Esterase Inhibitor:

(1A) carbamate compound: alanycarb, aldicarb, aldoxycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, 3,5-xylyl methylcarbamate (XMC), and xylylcarb

(1B) organo phosphorus compound: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diamidafos, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, DSP, EPN, ethion, ethoprophos, etrimnfos, famphur, fenamiphos, fenitrothion, fenthion, fonofos, fosthiazate, fosthictan, heptenophos, isamidofos, isazophos, isofenphos-methyl, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, mcethidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propaphos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, thionazin, triazophos, trichlorfon, vamidothion, dichlofenthion, imicyafos, isocarbophos, mesulfenfos, and flupyrazofos

2. GABA Receptor (Chloride Channel) Inhibitor

(2A) cyclodiene organic chloride-based compound: chlordane, endosulfan, and gamma-BCH

(2B) phenylpyrazole-based compound: acetoprol, ethiprole, fipronil, pyrafluprole, pyriprole, and RZI-02-003 (code number)

3. Preparation Acting on Sodium Channel

(3A) pyrethroid-based compound: acrinathrin, allethrin [including d-cis-trans and d-trans], bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, and cyfluthrin [including beta-], cyhalothrin [including gamma- and lambda-], cypermethrin [including alpha-, beta-, theta-, and zeta-], cyphenothrin [including (1R)-trans-isomers], deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, and tau-fluvalinate [including tau-], halfenprox, imiprothrin, metofluthrin, permethrin, and phenothrin [including (1R)-trans-isomer], prallethrin, profluthrin, pyrethrine, resmethrin, RU 15525 (code number), silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin, ZXI8901 (code number), fluvalinate, tetramethylfluthrin, and meperfluthrin

(3B) DDT-based compound: DDT, methoxychlor

4. Nicotinic Acetylcholine Receptor Agonist/Antagonist

(4A) neonicotinoid-based compound: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam

(4B) nicotine-based compound: nicotine-sulfate

5. Nicotinic Acetylcholine Receptor Allosteric Activator

spinosyn-based compound: spinctoram and spinosad

6. Chloride Channel Activating Preparation

avermectin, milbemycin-based compound: abamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, and polynactins

7. Juvenile Hormone Preparation

diofenolan, hydroprene, kinoprene, methothrin, fenoxycarb, and pyriproxyfen

8. Preparation with Non-Specific Mode of Action (Multiple Mode of Action)

1,3-dichloropropene, DCIP, ethylene dibromide, methyl bromide, chloropicrin, and sulfuryl fluoride

9. Feeding Inhibitor

pymetrozine, flonicamid and pyrifluquinazon

10. Mite Growth Controlling Agent

clofentezine, diflovidazin, hexythiazox, and etoxazole

11. Preparation for Disrupting Insect Intima

BT preparation:

12. ATP Biosynthesis Enzyme Inhibitor

diafenthiuron;

organo tin compound: azocyclotin, cyhexatin, and fenbutatin oxide;

propargite, tetradifon

13. Uncoupler

chlorfenapyr and DNOC

14. Preparation for Blocking Nicotinic Acetylcholine Channel

nereistoxin-based compound: bensultap, cartap, thiocyclam, and thiosultap

15. Chitin Biosynthesis Inhibitor (Type 0)

benzoylurea-based compound: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lifenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and fluazuron

16. Chitin Biosynthesis Inhibitor (Type 1)

buprofezin

17. Molting Inhibitor (for Diptera)

cyromazine

18. Ecdysone Agonist (for Promoting Molting)

diacylhydrazine-based compound: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide

19. Octopamine Agonist

amitraz

20. Mitochondrial Electron Transport Chain (Complex III) Inhibitor

cyflumetofen, hydramethylnon, acequinocyl, fluacrypyrim, and cycnopyrafen

21. Mitochondrial Electron Transport Chain (Complex 1) Inhibitor

METI acaricides: fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, and tolfenpyrad

others: rotenone

22. Sodium Channel Inhibitor

indoxacarb and metaflumizon

23. Lipid Biosynthesis Inhibitor

tetronic-based insecticides/acaricides: spirodiclofen, spiromesifen, and spirotetramat

24. Mitochondrial Electron Transport Chain (Complex IV) Inhibitor

aluminium phosphide, phosphine, zinc phosphide, calcium cyanide, and phosphine

25. Neuronal Inhibitor Preparation (Unknown Mode of Action)

bifenazate

26. Aconitase Inhibitor

sodium fluoroacetate

27. Preparation Acting on Ryanodine Receptor

chlorantraniliprole, flubendiamide and cyantraniliprole

28. Other Preparations (Unknown Mode of Action)

azadirachtin, amidoflumet, benclothiaz, benzoximate, bromopropylate, chinomethionat, CL900167 (code number), cryolite, dicofol, dicyclanil, dienochlor, dinobuton, fenbutatin oxide, fenothiocarb, fluensulfone, flufencrim, flusulfamide, karanjin, metham, methoprene, methoxyfenozide, methyl isothiocyanate, pyridalyl, pyrifluquinazon, sulcofuron-sodium, sulflramid, and sulfoxaflor

29. Synergistic Agent

piperonyl butoxide and DEF.

Hereinafter, production methods of the compound of Formula 1 according to the compound of the invention, formulation examples, and applications will be described in detail with reference to Examples below. However, the invention is not limited to these Examples in any way. In the description below, “%” means “percent by weight” and “parts” means “parts by weight”.

Example 1 Production of 6-(2-hydroxy-6-oxo cyclohexa-1-enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione (Compound No. I-50) (1) Production of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride

0.93 g (3.76 mmol) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid and 0.72 g (5.64 mmol) of oxalyl chloride were dissolved in dichloromethane (20 ml). To the mixture, a drop of N,N-dimethylformamide was added and stirred at room temperature for 2 hours. The reaction solution was concentrated to obtain 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

(2) Production 6-(2-hydroxy-6-oxo cyclohexa-1-enecarbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H,4H)-dione

0.63 g (5.64 mmol) of 1,3-cyclohexanedione and 0.57 g (5.64 mmol) of triethylamine were dissolved in dichloromethane (20 ml) under ice cooling. To the mixture, the dichloromethane solution (10 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride produced from the above (1) was slowly added dropwise, and stirred for 30 minutes under ice cooling. The reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (20 ml), added with 0.57 g (5.64 mmol) of triethylamine and 0.03 g (0.38 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. After concentration under reduced pressure, the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.36 g of the target compound (yield 28%).

Melting point: 182 to 185° C.

Example 2 Production of 6-(5-hydroxy-1-methyl-1H-pyrazole-4-carbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione (Compound No. II-50)

1.50 g (6.07 mmol) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid and 1.16 g (9.10 mmol) of oxalyl chloride were dissolved in dichloromethane (30 ml). To the mixture, a drop of N,N-dimethylformamide was added and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

Next, 1.22 g (9.10 mmol) of 1-methyl-5-hydroxypyrazole hydrochloride and 1.53 g (15.17 mmol) of triethylamine were added to dichloromethane (30 ml) under ice cooling. To the mixture, the dichloromethane solution (15 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride was slowly added dropwise, and stirred for 30 minutes. The reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (30 ml), added with 0.92 g (9.10 mmol) of triethylamine and 0.05 g (0.61 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. The reaction mixture was concentrated under reduced pressure, and then the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.40 g of the target compound (yield 20%).

Melting point: 197 to 199° C.

Example 3 Production of 6-(2-hydroxy-4-oxobicyclo[3.2.1]octa-2-en-yl carbonyl]-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione (Compound No. III-50)

1.00 g (4.04 mmol) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid and 1.03 g (8.09 mmol) of oxalyl chloride were dissolved in dichloromethane (20 ml). To the mixture, a drop of N,N-dimethylformamide was added and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to obtain 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride as a pale yellow oily substance.

Next, 0.83 g (6.07 mmol) of bicyclo[3.2.1]octane-2,4-dione and 0.61 g (6.07 mmol) of triethylamine were dissolved in dichloromethane (20 ml) under ice cooling. To the solution, the dichloromethane solution (10 ml) of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl chloride that is prepared previously was slowly added dropwise. After stirring for 30 minutes under ice cooling, the reaction mixture was extracted with chloroform, and the organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residues obtained were dissolved in acetonitrile (20 ml), added with 0.61 g (6.07 mmol) of triethylamine and 0.03 g (0.4 mmol) of acetone cyanohydrin, and refluxed for 30 minutes under heating. The reaction mixture was concentrated under reduced pressure, and then the residues were dissolved in water and washed with ethyl acetate. The aqueous layer was acidified by using citric acid, extracted with chloroform, dried over magnesium sulfate, and concentrated under reduced pressure. The crystals obtained were washed with methanol to obtain 0.70 g of the target compound (yield 47%).

Melting point: 163 to 165° C.

Example 4 Production of 1-isopropyl-4-(2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl carbonyl)-1H-pyrazole-5-yl propane-1-sulfonate (Compound No. II-267)

0.85 g (2.60 mmol) of 6-(5-hydroxy-1-isopropyl-1H-pyrazol-4-yl carbonyl)-2-methyl-4-phenyl-1,2,4-triazine-3,5(2H, 4H)-dione was dissolved in 20 ml of dichloromethane. To the solution, 0.27 g (2.60 mmol) of triethylamine and 0.37 g (2.60 mmol) of 1-propane sulfonyl chloride were added at room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residues were purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.71 g of the target compound (yield 63%).

Melting point: 51 to 53° C.

Example 5 Production of 2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-53) (1) Production of diethyl 2-(2-methylhydrazono) malonate

5.00 g (0.0287 mol) of diethyl ketomalonate was dissolved in 30 ml ethanol. To the solution, 1.45 g (0.0316 mol) of methyl hydrazine was added and stirred for 7 hours at 60° C. followed by further stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 5.28 g of the target compound (yield 91%).

(2) Production of ethyl 4-(4-chlorophenyl)-2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g (9.89 mmol) of DBU were dissolved in 50 ml of tetrahydrofuran. To the solution, the tetrahydrofuran (10 ml) solution of 4-chlorophenyl isocyanate (3.34 g, 21.7 mmol) was slowly added dropwise at room temperature, and stirred over night. The reaction mixture was concentrated under reduced pressure, and the residues were extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to obtain 2.00 g of the target compound (yield 65%).

(3) Production of 2-methyl-3,5-dioxo-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

2.00 g (6.46 mmol) of ethyl 2-methyl-4-(4-chlorophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was stirred at room temperature for 2 days in a mixed solvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reaction mixture was concentrated under reduced pressure to obtain 1.88 g of the target compound (yield, quantitative).

Melting point: 234 to 236° C.

Example 6 Production of 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-1) (1) Production of 2-methylsemicarbazide

13 g (282.1 mmol) of methyl hydrazine was dissolved in 60 ml of tetrahydrofuran. To the solution, 25 g (217 mmol) of trimethylsilyl isocyanate was slowly added dropwise at 0° C. and further stirred for 1 hour. To the reaction mixture, 40 ml of methanol was added and stirred for 5 hours at 40° C. The reaction mixture was concentrated to obtain 18 g of 2-methyl semicarbazide as a pale yellow solid (yield 93%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

3.15 (3H, s), 3.80 (2H, br), 5.61 (2H, br)

(2) Production of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

35.2 g (202 mmol) of diethyl ketomalonate and 18 g (202 mmol) of 2-methyl semicarbazide were dissolved in 200 ml ethanol, and then refluxed under heating for 36 hours. The reaction solution was concentrated to obtain 31 g of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester as a white solid (yield 78%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

1.39 (3H, t, J=7.1 Hz), 3.72 (3H, s), 4.42 (2H, q, J=7.1 Hz), 9.38 (1H, br)

(3) Production of Ethyl 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.0 g (10.0 mmol) of ethyl 2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester, 1.9 g (13.5 mmol) of potassium carbonate, and 1.8 g (12.5 mmol) of methyl iodide were added to 20 ml of N,N-dimethylformamide, and stirred for 2 hours at 60° C. Upon the completion of the reaction, the reaction solution was added with water, and then extracted with ethyl acetate. The organic layer obtained was dried over anhydrous magnesium sulfate and concentrated to obtain 1.8 g of ethyl 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester (yield 86%).

¹H-NMR (CDCl₃, TMS) δ(ppm):

1.40 (31, t, J=7.1 Hz), 3.38 (3H, s), 3.74 (3H, s), 4.42 (2H, q, J=7.1 Hz)

(4) Production of 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

1.8 g (8.41 mmol) of ethyl 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was stirred at room temperature for 24 hours in a mixed solvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reaction solution was concentrated to obtain 1.40 g of 2,4-dimethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid as a white solid (yield 90%).

Melting point: 220 to 223° C.

¹H-NMR (CDCl₃, TMS) δ(ppm):

3.48 (3H, s) 3.88 (3H, s)

Example 7 Production of 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-259) (1) Production of ethyl 3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

9.0 g (0.0517 mol) of diethyl ketomalonate and 7.81 g (0.0517 mol) of 2-phenyl semicarbazide were stirred in 50 ml xylene for 1 hour at 100° C. The reaction mixture was refluxed under heating, and by adding sodium methoxide (8.37 g, 0.155 mol) in small portions, the reaction was completed. After cooling to room temperature, the reaction mixture was neutralized with 1 N aqueous hydrochloric acid solution, extracted with ethyl acetate, and dried over magnesium sulfate. The reaction mixture was concentrated under reduced pressure and the residues were isolated and purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 6.18 g of the target compound (yield 46%).

(2) Production of ethyl 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

1.50 g (5.74 mmol) of ethyl 3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was dissolved in 30 ml of N,N-dimethylformamide, added with 60% sodium hydride (0.23 g, 5.74 mmol) under ice cooling, and further stirred for 30 minutes. The mixture was added with ethyl iodide (0.90 g, 5.74 mmol) and stirred. After raising to room temperature, an aqueous solution of ammonium chloride was added to terminate the reaction. The resultant was extracted with diethyl ether, dried over magnesium chloride, and concentrated under reduced pressure. The residues were purified by silica gel column chromatography to obtain 1.33 g of the target compound (yield 80%).

(3) Production of 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

1.30 g (4.49 mmol) of ethyl 2-ethyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was dissolved in 30 ml ethanol, added with a 25% aqueous solution of sodium hydroxide (1.29 g, 8.09 mmol), and stirred overnight. After dilution by adding water, the aqueous layer was washed with diethyl ether. The aqueous layer was acidified by adding 6 N aqueous hydrochloric acid solution, and then extracted with ethyl acetate. After drying over magnesium sulfate and concentration under reduced pressure, 1.10 g of the target compound was obtained (yield 94%).

Example 8 Production of 2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-265) (1) Production of ethyl 2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.00 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 1.50 g (9.89 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolved in 50 ml of tetrahydrofuran. To the solution, the tetrahydrofuran (10 ml) of ethylisothiocyanate (1.58 g, 21.7 mmol) was slowly added dropwise and stirred overnight. The reaction mixture was concentrated under reduced pressure, extracted with ethyl acetate, washed with water, and dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 2.20 g of the target compound (yield 97%).

(2) Production of 2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

2.30 g (0.01 mol) of ethyl 2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was stirred overnight at room temperature in a mixed solvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reaction mixture was concentrated under reduced pressure to obtain 2.01 g of the target compound (yield; quantitative).

Example 9 Production of 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-72) (1) Production of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.0 g (9.89 mmol) of diethyl 2-(2-methylhydrazono) malonate and 3.3 g (21.8 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were dissolved in 20 ml of tetrahydrofuran. To the solution, 4.9 g (20.8 mmol) of phenyl-2-cyanophenylcarbamate was added at room temperature and stirred for 1 hour at the same temperature. After that, the mixture was refluxed under heating for 3 hours. The reaction solution was concentrated and the residues were extracted with ethyl acetate. The organic layer obtained was washed with water and an aqueous solution of citric acid in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 2.3 g of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester (yield 78%).

¹H-NMR (CDCl₃, TMS) (ppm):

1.40 (3H, t, J=7.1 Hz), 3.81 (3H, s), 4.45 (2H, q, J=7.1 Hz), 7.39 (1H, d, J=8.0 Hz), 7.67-6.64 (1H, m), 7.75-7.80 (1H, m), 7.85 (1H, d, J=7.6 Hz)

(2) Production of 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

2.3 g (7.65 mmol) of ethyl 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester was stirred for 24 hours at room temperature in a mixed solvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reaction solution was concentrated under reduced pressure to obtain 1.8 g of 2-methyl-3,5-dioxo-4-(2-cyanophenyl)-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid as a white solid (yield 90%).

Melting point: 213 to 215° C.

¹H-NMR (DMSO-d₆, TMS) δ(ppm):

3.65 (3H, s), 7.67 (1H, d, J=8.0 Hz), 7.70-7.75 (1H, m), 7.90-7.96 (1H, m), 8.09 (1H, d, J=7.4 Hz), 14.02 (1H, br)

Example 10 Production of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid (Compound No. V-50) (1) Production of ethyl 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester

2.0 g (9.89 mmol) of diethyl 2-oxomalonate and 0.04 g (0.2 mmol) of p-toluene sulfonic acid were dissolved in 50 ml of toluene. To the solution, 2.5 g (15.2 mmol) of 1-methyl-N-phenylhydrazine carboxamides was added at room temperature, and then stirred for 2 hours with reflux under heating. The reaction mixture was cooled to room temperature and added with 0.08 g (0.5 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by stirring at room temperature for two hours. The reaction solution was washed with water and dried over magnesium sulfate. The solvent was distilled off to obtain ethyl 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester.

(2) Production of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid

Ethyl 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid ester produced from the above (1) was stirred for 24 hours at room temperature in a mixed solvent of acetic acid (30 ml) and conc. hydrochloric acid (30 ml). The reaction mixture was concentrated under reduced pressure, extracted with a saturated aqueous solution of sodium hydrogen carbonate, washed with ethyl acetate, and then adjusted to be weakly acidic by using diluted hydrochloric acid. After that, the mixture was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was distilled off to obtain 2.6 g of 2-methyl-3,5-dioxo-4-phenyl-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxylic acid as a white solid (2-step yield 70%).

Melting point: 195 to 198° C.

¹H-NMR (DMSO-d₆, TMS) δ(ppm):

3.59 (3H, s), 7.29-7.31 (2H, m), 7.43-7.54 (3H, m), 13.64 (1H, bs)

Physical property values (melting point or refractive index) of the compound of the invention represented by Formula 1, which has been synthesized according to the above Examples, are shown in Table 68 to Table 70 including above Examples. Herein, * means refractive index.

TABLE 68 Compound Melting Point(° C.) or No. Refractive Index(n_(D) ²⁰) I-2 87-89 I-3 1.5530* I-5 1.5630* I-9 1.5380* I-10 124-125 I-11 97-98 I-14 126-129 I-16 116-118 I-19 132-134 I-27 1.5460* I-41 1.5495* I-43  98-101 I-47 155-157 I-50 182-185 I-51 184-185 I-52 187-190 I-53 182-183 I-54 174-176 I-55 209-212 I-56 181-183 I-57 135-136 I-58 198-199 I-59 190-193 I-60 190-191 I-61 186-187 I-62 137-139 I-63 166-169 I-64 89-92 I-65 184-187 I-66 151-152 I-67 174-177 I-68 208-210 I-71 130-131 I-72 166-169 I-73 181-184 I-74 108-111 I-75 173-176 I-76 242-245 I-77 192-194 I-78 149-151 I-79 161-163 I-80  98-101 I-81 158-161 I-82 212-215 I-83 191-194 I-84 124-127 I-85 235-238 I-86 199-202 I-87 197-198 I-88 160-163 I-89 190-193 I-90 164-166 I-91 89-91 I-92 245-247 I-93 168-169 I-94 155-157 I-96 151-153 I-98 155-157 I-99 178-181 I-105 186-188 I-106 228-231 I-107 212-215 I-108 167-169 I-109 166-168 I-110 151-152 I-111 196-199 I-115 144-147 I-116 176-179 I-117 140-143 I-118 140-143 I-119 191-194 I-120 191-194 I-125 148-151 I-126 126-129 I-127 237-240 I-128 217-220 I-129 155-158 I-131 204-205 I-134 215-217 I-135 152-154 I-136 156-157 I-137 154-157 I-138 123-126 I-149 175-178 I-155 196-199 I-167 183-185 I-169 178-180 I-170 213-215

TABLE 69 Compound Melting Point(° C.) or No. Refractive Index (n_(D) ²⁰) I-179 215-218 I-182 159-161 I-183 138-141 I-184 100-103 I-185 108-111 I-187 180-183 I-189 190-193 I-198 135-137 I-199 169-170 I-202 161-162 I-203 188-191 I-204 201-204 I-205 87-90 I-259 150-153 I-260 152-154 I-261 190-193 I-262 103-106 I-263 174-176 I-265 164-167 I-268 201-204 I-269 112-115 I-270 172-175 I-271 251-254 I-272 204-207 I-274 101-103 I-275 89-92 I-276 167-170 I-277 96-99 I-278  98-101 I-279 218-220 I-280 168-171 I-281 146-147 I-282 148-151 I-283 172-175 I-284 160-162 I-285 149-152 I-286 88-91 I-287 155-158 I-288 94-97 I-289 215-218 I-290 138-141 I-291 194-197 I-292 167-169 I-293 158-160 I-294 113-115 I-295 1.5360* I-296 1.5300* I-297 89-92 I-298 148-150 I-299 212-215 I-300 203-205 I-301 274-277 I-302 222-224 I-303 62-65 I-304 148-151 I-307 58-61 I-328 58-61 I-463 131-134 I-464 168-170 I-465 211-213 I-466 89-92 I-467 211-214 I-468 128-130 I-469 172-174 I-470 147-148 I-471 1.5620* I-472 162-164 I-473 143-146 I-474 70-73 I-475 83-86 I-476 191-193 I-477 149-151 I-478 1.5270* I-479 1.5450* I-480 179-181 II-50 197-199 II-267 51-53 III-50 163-165 III-62 158-159 VI-1 151-154 VI-5 145-148 VI-6 145-146 VI-7 163-166 VI-65 93-96 VI-97 158-160

Compound number and ¹H-NMR data (standard; TMS, δ (ppm) value) are given below. Data without a name of solvent are measured by using CDCl₃.

Compound No. I-1:

2.04-2.10 (2H, m), 2.45-2.49 (2H, m), 2.76-2.80 (2H, m), 3.56 (3H, s), 3.65 (3H, s) 16.05 (1H, br)

Compound No. I-3:

0.92 (3H, t, J=6.00 Hz), 1.69 (2H, q, J=6.00 Hz), 2.03-2.11 (2H, m), 2.45-2.49 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.89 (2H t, J=6.00 Hz), 16.05 (1H, br)

Compound No. I-4:

1.49 (6H, d, J=6.00 Hz), 2.03-2.11 (2H, m), 2.44-2.49 (2H, m), 2.74-2.79 (2H, m), 3.61 (3H, s), 5.07 (1H, sept, J=6.00 Hz), 16.08 (1H, br)

Compound No. I-5:

0.95 (3H, t, J=72 Hz), 1.32-1.43 (2H, m), 1.59-1.68 (2H, m), 2.03-2.10 (2H, m), 2.45-2.49 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.92 (2H, t, J=6.9 Hz), 16.05 (1H, br)

Compound No. I-9:

0.88 (3H, t, J=6.6 Hz), 1.20-1.40 (6H, m), 1.58-1.64 (2H, m), 2.03-2.12 (2H, m), 2.44-2.48 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.89-3.94 (2H, m), 16.04 (1H, br)

Compound No. I-27:

1.65 (3H, t, J=3.00 Hz), 2.03-2.09 (2H, m), 2.31-2.36 (2H, m), 2.44-2.49 (2H, m), 2.74-2.79 (2H, m), 3.64 (3H, s), 4.01 (2H, t, J=6.00), 16.00 (1H br)

Compound No. 1-41:

1.89-1.97 (2H, m), 2.04-2.11 (2H, m), 2.44-2.48 (2H, m), 3.31 (3H, s), 3.44 (2H, t, J=6.0 Hz), 3.64 (3H, s), 4.03 (2H, t, J=7.0 Hz), 16.04 (1H, br)

Compound No. I-75:

2.05-2.1 (2H, m), 2.45-2.49 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s), 7.05-7.09 (1H, m), 7.14-7.21 (1H, m), 7.24-7.33 (1H, m), 15.99 (1H, s)

Compound No. I-76:

2.04-2.09 (2H, m), 2.46-2.50 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s), 6.88-6.96 (3H, m), 15.97 (1H, s)

Compound No. I-77:

2.03-2.09 (2H, m), 2.45-2.49 (2H, m), 2.75-2.78 (2H, m), 3.71 (3H, s), 7.11-7.14 (1H, m), 7.18-7.33 (2H, m), 15.95 (1H, s)

Compound No. I-79:

2.04-2.10 (2H, m), 2.45-2.50 (2H, m), 2.75-2.79 (2H, m), 3.70 (3H, s), 7.10-7.24 (3H, m), 15.96 (1H, s)

Compound No. I-80:

2.01-2.08 (2H, m), 2.46-2.49 (2H, m), 2.75-2.78 (2H, m), 3.71 (3H, s), 7.05-7.08 (2H, m), 7.40-7.48 (1H, m), 15.93 (1H, s)

Compound No. I-81:

2.05-2.08 (2H, m), 2.45-2.50 (2H, m), 2.75-2.80 (2H, m), 3.69 (3H, s), 7.14-7.19 (1H, m), 7.43 (1H, d, J=25), 7.57 (1H, d, J=8.5), 15.97 (1H, s)

Compound No. I-295:

0.85-0.89 (3H, m), 1.26-1.32 (10H, m), 1.57-1.65 (2H, m), 2.05-2.12 (2H, m), 2.44-2.49 (2H, m), 2.75-2.79 (2H, m), 3.64 (3H, s), 3.88-3.93 (2H, m), 16.04 (1H, br)

Compound No. I-296:

0.85-0.90 (3H, m), 1.25-1.36 (14H, m), 1.59-1.69 (2H, m), 2.05-2.09 (2H, m), 2.44-2.49 (2H, m), 2.74-2.79 (2H, m), 3.64 (3H, s), 3.88-3.93 (2H, m), 16.04 (1H, br)

Compound No. I-306:

0.96 (3H, t, J=7.15), 1.39-1.46 (2H, m), 1.69-1.71 (2H, m), 2.05-2.09 (2H, m), 2.44-2.48 (2H, m), 4.01 (2H, t, J=7.69), 7.32-7.36 (2H, m), 7.56-759 (1H, m), 7.83-7.88 (1H, m), 8.61-8.63 (1H, m), 16.05 (1H, br)

Compound No. I-308:

0.88-0.92 (3H, m), 0.35-0.37 (4H, m), 0.79-1.82 (2H, m), 2.03-2.07 (2H, m), 2.44-2.49 (2H, m), 2.73-2.78 (2H, m), 4.01 (2H, t, J=7.69), 7.28-7.30 (2H, m), 7.43-7.53 (3H, m), 16.06 (1H, br)

Compound No. I-339:

1.84-2.11 (4H, m), 2.44-2.48 (2H, m), 2.74-2.78 (2H, m), 3.64 (3H, s), 3.69-3.92 (3H, m), 4.07-4.34 (2H, m), 16.04 (1H, br)

Compound No. I-462:

1.30 (3H, t, J=7.66), 2.03-2.07 (2H, m) 2.45-2.49 (2H, m), 2.69-2.77 (4H, m), 3.68 (3H, s), 7.28-7.30 (1H, m), 7.77-7.73 (1H, m), 8.51 (1H, s), 16.03 (1H, br)

Physical property values of the production intermediate [13a] and [3b] are given in Table 70 and Table 71.

TABLE 70 Compound No. Melting Point (° C.) IV-116 111-114 IV-117 100-102 IV-118 118-121 IV-136 131-133 IV-137 102-105 IV-138 122-125 IV-182 107-108 IV-185 50-53 IV-197 122-125 IV-259 84-86 IV-260 107-109 IV-261 132-135 IV-275 102-103 IV-276 46-49 IV-278 171-172 IV-280 137-140 IV-284 136-137 IV-285 112-114 IV-287 140-142 IV-288 101-102 IV-290 124-127 IV-291 137-138

TABLE 71 Compound No. Melting Point(° C.) V-1 220-223 V-2 165-168 V-3 113-115 V-4 122-125 V-5  98-100 V-9  99-102 V-10 127-129 V-11 82-84 V-14 142-144 V-16 155-158 V-27 114-117 V-41 90-91 V-43 145-146 V-47 144-147 V-50 195-198 V-51 154-157 V-52 118-120 V-53 234-236 V-54 95-98 V-55 95-98 V-56 212-215 V-57 150-152 V-58 196-199 V-60 145-146 V-61 173-174 V-66 164-166 V-67 200-203 V-68 206-209 V-72 213-215 V-73 221-224 V-87 162-165 V-88 227-230 V-89 184-186 V-90 156-159 V-91 179-181 V-92 207-210 V-93 220-223 V-99 166-169 V-105 169-171 V-106 231-234 V-107 166-169 V-108 153-156 V-109 197-198 V-110 194-197 V-111 187-190 V-115 188-191 V-119 205-208 V-125 173-175 V-127 135-138 V-128 186-188 V-129 198-201 V-131 201-204 V-135 224-227 V-149 216-218 V-155 229-231 V-167 211-212 V-169 199-202 V-170 177-180 V-179 237-240 V-184 158-161 V-189 200-201 V-202 200-203 V-203 164-167 V-204 199-202 V-268 201-204 V-269 155-157 V-270 184-187 V-271 208-211 V-272 100-102 V-273 202-205 V-275 166-169 V-282 193-196 V-283 186-189 V-291 175-178 V-294 204-207 V-295 105-107 V-296 106-108 V-297 176-179 V-298 145-146 V-299 241-244 V-300 245-248 V-301 259-261 V-302 211-212 V-303 152-155 V-304 140-143 V-305 166-167 V-328 143-146 V-358 240-243 V-359 91-94 V-360 240-242 V-361 155-158 V-362 148-151 V-363 189-192 V-364 213-216 V-365 75-78 V-366 218-221 V-367 192-195 V-368 153-156 V-369 111-113 V-370 100-103 V-371 80-83

Compound number and ¹H-NMR data (standard; TMS, δ (ppm) value) for the production intermediates are given below. Data without a name of solvent are measured by using CDCl₃.

Compound No. IV-19:

1.19-1.41 (3H, m), 1.39 (3H, t, J=5.3 Hz), 1.56-1.66 (3H, m), 1.83-1.87 (2H, m), 2.37 (2H, dq, J=3.3 Hz, 12.1 Hz), 3.68 (3H, s), 4.41 (2H, q, J=7.1 Hz), 4.73 (1H, tt, J==3.3 Hz, 12.1 Hz)

Compound No. IV-50:

1.39 (3H, t, J=7.1 Hz), 3.71 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.24-7.26 (2H, m), 7.49-7.57 (3H, m)

Compound No. IV-53:

1.39 (3H, t, J=5.3 Hz), 3.77 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.18 (2H, d, J=6.4 Hz), 7.49 (2H, d, J=6.4 Hz)

Compound No. IV-56:

1.39 (3H, t, J=7.1 Hz), 3.77 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.20-7.22 (4H, m)

Compound No. IV-59:

1.39 (3H, t, J=7.1 Hz), 2.41 (3H, s), 3.77 (3H, s), 4.42 (2H, q, J=7.1 Hz), 7.10 (2H, d, J=8.3 Hz), 7.31 (2H, d, J=8.3 Hz)

Compound No. IV-62:

1.39 (3H, t, J=7.1 Hz), 3.76 (3H, s), 3.84 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.01 (2H, d, J=9.0 Hz), 7.14 (2H, d, J=9.0 Hz)

Compound No. IV-63:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.30 (1H, d, J=7.7 Hz), 7.67 (1H, t, J=7.7), 7.74 (1H, dt, J=1.1 Hz, 7.7 Hz), 7.84 (1H, dd, J=1.1 Hz, 7.7 Hz)

Compound No. IV-64:

1.40 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.44 (2H, q, J=7.1 Hz), 7.44 (1H, d, J=8.0 Hz), 7.54 (1H, s), 7.66 (1H, t, J=8.0 Hz), 7.75 (1H, d, J=8.0 Hz)

Compound No. IV-65:

1.40 (3H, t, J=5.3 Hz), 3.79 (3H, s), 4.44 (2H, q, J=5.3 Hz), 7.39 (2H, d, J=6.2 Hz), 7.79 (2H, d, J=6.2 Hz)

Compound No. IV-71:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.43 (2H, q, J=7.1 Hz), 7.28 (2H, d, J=8.5 Hz), 7.36 (2H, d, J=8.5 Hz)

Compound No. IV-74:

1.39 (3H, t, J=7.1 Hz), 3.78 (3H, s), 4.44 (2H, q, J=7.1 Hz), 7.39 (2H, dd, J=1.9 Hz, 6.6 Hz), 7.82 (2H, dd, J=1.9 Hz, 6.6 Hz)

Compound No. IV-78:

1.40 (3H, t, J=7.1 Hz), 3.79 (3H, s), 4.43 (2H, q, J=7.1 Hz), 6.99-7.05 (2H, m), 7.22-7.28 (1H, m)

Compound No. IV-93:

1.39 (3H, t, J=7.1 Hz), 3.77 (3H, s), 3.78 (6H, s), 4.43 (2H, q, J=7.1 Hz), 6.35 (2H, d, J=2.2 Hz), 6.55 (1H, t, J=2.2 Hz)

Compound No. IV-96:

1.39 (3H, t, J=7.1 Hz), 3.76 (6H, s), 3.83 (3H, s), 4.42 (2H, q, J=7.1 Hz), 6.55-6.59 (2H, m), 7.05 (1H, d, J=9.1 Hz)

Compound No. IV-134:

1.40 (3H, t, J=5.3 Hz), 3.77 (3H, s), 3.79 (3H, s), 4.43 (2H, q, J=5.3 Hz), 6.97 (1H, d, J=6.8 Hz), 7.17 (1H, d, J=2.0 Hz), 7.41 (1H, dd, J=2.0 Hz, 6.8 Hz)

Compound No. IV-179:

1.39 (3H, t, J=5.3 Hz), 3.77 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.32 (1H, d, J=5.7 Hz), 7.46 (1H, dd, J=5.7 Hz, 3.7 Hz), 7.92 (1H, dt, J=1.1 Hz, 5.7 Hz), 8.68 (1H, dt, J=3.7 Hz, 1.1 Hz)

Compound No. IV-198:

1.40 (3H, t, J=5.3 Hz), 3.78 (3H, s), 4.43 (2H, q, J=5.3 Hz), 7.07-7.12 (2H, m), 7.42 (1H, dd, J=1.1 Hz, 4.0 Hz)

Compound No. IV-259:

1.39 (3H, t, J=7.1 Hz), 1.43 (3H, t, J=7.1 Hz), 4.17 (2H, q, J=7.1 Hz), 4.43 (2H, q, J=7.1 Hz), 7.21-7.26 (2H, m), 7.44-7.55 (3H, m)

Compound No. IV-260:

1.39 (31H, t, J=7.1 Hz), 1.43 (6H, d, J=6.8 Hz), 4.42 (2H, q, J=7.1 Hz), 5.01 (1H, p, J=6.8 Hz), 7.22-7.26 (2H, m), 7.46-7.55 (3H, m)

Compound No. IV-261:

1.40 (3H, t, J=7.1 Hz), 4.46 (2H, q, J=7.1 Hz), 7.23-7.26 (2H, m), 7.47 (1H, t, J=57.8 Hz), 7.51-7.66 (3H, m)

Compound No. IV-262:

1.39 (3H, t, J=7.1 Hz), 4.44 (2H, q, J=7.1 Hz), 7.26-7.60 (10H, m)

Compound No. IV-265:

1.40 (3H, t, J=7.1 Hz), 3.71 (3H, s), 4.05 (3H, s), 4.44 (2H, q, J=7.1 Hz)

Compound No. IV-286:

1.19-1.17 (6H, dd, J=7.0 Hz, J=2.2 Hz), 1.41-1.37 (3H, t, J=7.1 Hz), 2.65-2.58 (1H, sept., J=7.0 Hz), 3.78 (3H, s), 4.46-4.39 (2H, q, J=7.0 Hz), 7.05-7.03 (1H, d, J=8.0 Hz), 7.33-7.29 (1H, m), 7.47-7.46 (2H, d, J=4.0 Hz)

Compound No. V-19: (Solvent for Measurement: DMSO-d₆)

1.09-1.34 (3H, m), 1.59-1.64 (2H, m), 0.76-1.80 (2H, m), 2.22 (2H, dq, J=3.3 Hz, 12.3 Hz), 3.51 (3, s), 4.54 (1H, tt, J=3.3 Hz, 12.3 Hz), 13.53 (1H, bs)

Compound No. V-50: (Solvent for Measurement: DMSO-d₆)

3.59 (3H, s), 7.29-7.31 (2H, m), 7.43-7.54 (3H, m), 13.64 (1H, bs)

Compound No. V-53: (Solvent for Measurement: DMSO-d₆)

3.59 (3H, s), 7.35 (2H, dd, J=1.6 Hz, 5.0 Hz), 7.59 (2H, dd, J=1.6H, 5.0 Hz), 13.66 (1H, bs)

Compound No. V-56: (Solvent for Measurement: DMSO-d₆)

3.59 (3H, s), 7.34-7.37 (4H, m), 13.65 (1H, bs)

Compound No. V-59: (Solvent for Measurement: DMSO-d₆)

2.36 (3H, s), 3.58 (3H, s), 7.17 (2H, d, J=8.3 Hz), 7.30 (2H, d, J=8.3 Hz), 13.62 (1H, bs)

Compound No. V-62: (Solvent for Measurement: DMSO-d₆)

3.39 (3H, s), 3.74 (3H, s), 6.93 (2H, d, J=9.0), 7.39 (2H, d, J=9.0 Hz), 9.54 (1H, bs)

Compound No. V-63: (Solvent for Measurement: DMSO-d₆)

3.62 (3H, s), 7.64 (1H, d, J=7.7 Hz), 7.75 (1H, t, J=7.68 Hz), 7.87-7.94 (2H, m), 13.90 (1H, bs)

Compound No. V-64: (Solvent for Measurement: DMSO-d₆)

3.41 (3H, s), 7.46 (1H, d, J=6.0 Hz), 7.60 (1H, t, J=6.0 Hz), 7.82 (1H, d, J=6.0 Hz), 7.97 (1H, s), 9.90 (1H, bs)

Compound No. V-65: (Solvent for Measurement: DMSO-d₆)

3.60 (3H, s), 7.58 (2H, d, J=8.3 Hz), 7.92 (2H, d, J=8.3 Hz), 13.69 (1H, bs) [0259]

Compound No. V-71: (Solvent for Measurement: DMSO-d₆)

3.59 (3H, s), 7.47 (2H, dt, J=9.3 Hz, 2.2 Hz), 7.54 (2H, d, J=9.3 Hz), 13.67 (1H, bs)

Compound No. V-75:

3.92 (3H, s), 7.03-7.06 (1H, m), 7.13-7.18 (1H, m), 7.35-7.41 (1H, m)

Compound No. V-76:

3.92 (3H, s), 7.85-7.87 (2H, m), 7.00-7.12 (1H, m)

Compound No. V-77:

3.94 (3H, s), 7.07-7.11 (1H, m), 7.29-7.31 (1H, m), 7.38-7.42 (1H, m)

Compound No. V-78: (Solvent for Measurement: DMSO-d₆)

3.61 (3H, s), 7.25-7.31 (1H, m), 7.49-7.58 (2H, m), 13.79 (1H, bs)

Compound No. V-79:

3.94 (3H, s), 7.05-7.07 (1H, m), 7.27-7.32 (2H, m)

Compound No. V-80:

3.94 (3H, s), 7.12-7.18 (2H, m), 7.52-7.61 (1H, m)

Compound No. V-81: (Solvent for Measurement: DMSO-d₆)

3.60 (3H, s), 7.37 (1H, d, J=8.5 Hz), 7.69 (1H, s), 7.82 (1H, d, J=7.7 Hz)

Compound No. V-82:

3.92 (3H, s), 7.20 (2H, s), 7.56 (1H, s)

Compound No. V-83:

3.93 (3H, s), 7.25 (1H, d, J=10.4), 7.44 (1H, t, J=8.0), 7.68 (1H, d, J=11.7)

Compound No. V-84:

3.93 (3H, s), 7.21 (1H, d, J=15.6), 7.45-7.48 (1H, m), 7.68 (1H, d, H=2.4 Hz)

Compound No. V-85:

3.93 (3H, s), 7.33 (1H, d, J=5.7), 7.49-7.58 (2H, m)

Compound No. V-86:

3.95 (3H, s), 7.45-7.56 (2H, m)

Compound No. V-93: (Solvent for Measurement: DMSO-d₆)

3.58 (3H, s), 3.74 (6H, s), 7.32 (2H, d, J=2.2 Hz), 6.59 (1H, t, J=2.2 Hz), 13.63 (1H, bs)

Compound No. V-96: (Solvent for Measurement: DMSO-d₆)

3.59 (3H, s), 3.73 (3H, s), 3.82 (3H, s), 7.62 (1H, dd, J=2.5 Hz, 8.8 Hz), 6.71 (1H, s), 7.16 (1H, d, J=8.5 Hz), 13.76 (1H, bs)

Compound No. V-134: (Solvent for Measurement: DMSO-d₆)

3.60 (3H, s), 3.76 (3H, s), 723 (1H, d, J=9.1 Hz), 7.43 (1H, d, J=2.8 Hz), 7.54 (1H, dd, J=2.8 Hz, 9.1 Hz), 13.84 (1H, bs)

Compound No. V-170: (Solvent for Measurement: DMSO-d₆)

3.58 (3H, s), 6.10 (2H, s), 6.78 (1H, dd, J=1.0 Hz, 6.2 Hz), 6.89 (1H, d, J=1.0 Hz), 7.01 (1H, d, J=6.2 Hz), 13.63 (1H, bs)

Compound No. V-179: (Solvent for Measurement: DMSO-d₆)

3.60 (3H, s), 7.49 (1H, d, J=7.1 Hz), 7.55 (1H, ddd, J=1.1 Hz, 5.0 Hz, 7.7 Hz), 8.05 (1H, dt, J=1.9 Hz, 7.7 Hz), 8.62 (1H, dd, J=1.1 Hz, 5.0 Hz)

Compound No. V-198: (Solvent for Measurement: DMSO-d₆)

3.57 (3H, s), 7.07-7.10 (2H, m), 7.63 (1H, dd, J=1.9 Hz, 5.2 Hz)

Compound No. V-259: (Solvent for Measurement: DMSO-d₆)

1.09 (3H, t, J=5.3 Hz), 3.96 (2H, q, J=5.3 Hz), 7.32-7.37 (2H, m), 7.45-7.54 (3H, m), 9.51 (1H, bs)

Compound No. V-261: (Solvent for Measurement: DMSO-d₆)

7.36-7.53 (5H, m), 7.82 (1H, t, J=42.9 Hz)

Compound No. V-265: (Solvent for Measurement: DMSO-d₆)

3.53 (3H, s), 3.90 (3H, s)

Compound No. V-268: (Solvent for Measurement: DMSO-d₆)

1.45 (3H, t), 3.91 (3H, s), 4.09 (2H, q), 7.04 (2H, d), 7.15 (2H, d) [0261]

<Formulation Example 1> Wettable Powder

10 parts of the compound (I-1), 0.5 parts of polyoxyethylene octylphenyl ether, 0.5 parts of sodium β-naphthalene sulfonate formalin condensate, 20 parts of diatomaceous earth, and 69 parts of clay were mixed and pulverized to give a wettable powder.

<Formulation Example 2> Flowable Agent

20 parts of roughly crushed compound (I-1) were dispersed in 69 parts of water, and added with 200 ppm of silicone AF-118N (trade name, manufactured by Asahi Kasei Corporation) while simultaneously adding 4 parts of polyoxyethylene styryl phenyl ether sulfonate and 7 parts of ethylene glycol. After mixing for 30 minutes by high-speed mixer, the mixture was pulverized using a wet-type pulverizer to give a flowable agent.

<Formulation Example 3> Emulsifiable Concentrate

30 parts of the compound (I-1), 60 parts of a mixture of xylene and isophorone (1:1 mixture), and 10 parts of a mixture of polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer, and alkylaryl sulfonate were mixed well to give an emulsifiable concentrate.

<Formulation Example 4> Granules

10 parts of the compound (I-1), 80 parts of extender in which talc and bentonite are mixed in ratio of 1 to 3, 5 parts of white carbon, and 5 parts of a mixture of polyoxyethylene sorbitan alkylate, polyoxyethylene alkylaryl polymer, and alkylaryl sulfonate were added with 10 parts of water. After kneading well, the resulting paste was extruded through a sieve (diameter; 0.7 mm) followed by drying. By cutting it to have length of 0.5 to 1 mm, granules were obtained.

Effect of the compounds of the invention is explained by way of following test examples.

<Test Example 1> Test for Determining Herbicidal Activity by Paddy Field Soil Treatment

A 100 cm² wide plastic pot was filled with a paddy field soil and, after watering and shuffling, seeds of each of Echinochloa oryzicola, Monochoria vaginalis, and Scirpus juncoides Rocxb. were sowed and watered to a depth of 3 cm. On the next day, the wettable powder obtained in view of Formulation example 1 was diluted with water and applied on water surface. The application amount was 1000 g of effective component per hectare. After that, the plants were cultivated in a greenhouse, and on day 21 after the treatment, evaluation was made by the criteria of Table 72 for determining the herbicidal effects. The results are shown in Table 73 to Table 76.

TABLE 72 Index Number Herbicidal Effects 10 100% of herbicidal effects (complete death) 9  90% or more and less than 100% of herbicidal effects 8  80% or more and less than 90% of herbicidal effects 7  70% or more and less than 80% of herbicidal effects 6  60% or more and less than 70% of herbicidal effects 5  50% or more and less than 60% of herbicidal effects 4  40% or more and less than 50% of herbicidal effects 3  30% or more and less than 40% of herbicidal effects 2  20% or more and less than 30% of herbicidal effects 1  10% or more and less than 20% of herbicidal effects 0  0% or more and less than 10% of herbicidal effects

TABLE 73 Compound Echinochloa No. oryzicola I-1 10 I-2 10 I-3 10 I-4 9 I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 9 I-19 10 I-27 10 I-41 8 I-43 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 8 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 8 I-83 10 I-84 10 I-85 10 I-86 10 I-87 9 I-88 10 I-89 10 I-90 9 I-91 10 I-92 10 I-93 8 I-96 8 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10 I-115 10 I-116 10 I-117 10 I-118 10 I-119 9 I-120 8 I-125 10 I-126 10 I-127 10 I-128 8 I-129 10 I-131 9 I-134 10 I-135 10 I-136 9 I-137 10 I-138 10 I-149 9 I-155 10 I-169 10 I-170 10 I-179 10 I-184 10 I-185 8 I-187 10 I-198 8 I-199 9 I-202 10 I-203 10 I-205 7 I-259 10 I-260 10 I-261 8 I-263 10 I-265 10 I-268 10 I-269 8 I-270 8 I-271 8 I-272 7 I-273 9 I-274 8 I-275 9 I-276 8 I-277 9 I-278 8 I-279 8 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-286 10 I-287 10 I-288 10 I-289 10 I-292 10 I-294 9 I-297 10 I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10 I-307 8 I-328 10 I-339 10 I-463 10 I-464 10 I-465 10 I-466 8 I-468 10 I-469 10 I-470 10 I-471 10 I-473 8 I-474 10 I-475 10 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 III-50 10 III-62 8 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 10 V-358 10 V-359 8 V-362 10 V-363 10 V-364 10 V-365 10 V-367 8 V-368 10 V-369 10 V-370 10 V-371 10

TABLE 74 Compound Monochoria No. vaginalis I-1 10 I-2 10 I-3 10 I-4 9 I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 9 I-19 10 I-27 10 I-41 8 I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 7 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-62 8 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-87 10 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10 I-115 10 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10 I-127 10 I-128 9 I-129 10 I-131 10 I-134 10 I-135 10 I-136 10 I-137 10 I-138 10 I-149 10 I-155 10 I-169 10 I-170 10 I-179 10 I-182 8 I-183 10 I-184 10 I-185 9 I-187 10 I-189 10 I-198 10 I-199 8 I-202 10 I-203 10 I-204 8 I-205 10 I-259 10 I-260 10 I-261 10 I-262 8 I-263 10 I-265 10 I-268 10 I-269 8 I-270 8 I-271 8 I-272 8 I-273 9 I-274 8 I-275 10 I-276 8 I-277 9 I-278 9 I-279 8 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-286 10 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10 I-292 10 I-293 10 I-294 9 I-297 10

TABLE 75 Compound Monochoria No. vaginalis I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10 I-306 9 I-307 9 I-308 8 I-328 10 I-339 10 I-462 10 I-463 10 I-464 10 I-465 10 I-466 10 I-467 10 I-468 10 I-469 10 I-470 10 I-471 10 I-472 10 I-473 10 I-474 10 I-475 10 I-476 10 I-477 10 I-478 10 I-479 10 II-50 8 II-267 8 III-50 10 III-62 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-291 8 V-300 10 V-358 10 V-359 10 V-360 10 V-361 10 V-362 10 V-363 10 V-364 10 V-365 10 V-366 10 V-367 10 V-368 10 V-369 10 V-370 10 V-371 10

TABLE 76 Compound S. juncoides No. Rocxb. I-1 10 I-2 10 I-3 10 I-4 10 I-5 10 I-9 8 I-10 10 I-11 10 I-14 10 I-16 10 I-19 10 I-27 10 I-41 10 I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-87 10 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-99 10 I-105 10 I-306 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10 I-115 10 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10 I-127 10 I-128 10 I-329 10 I-131 10 I-134 10 I-135 10 I-136 10 I-137 10 I-128 10 I-149 10 I-155 10 I-169 10 I-170 10 I-179 10 I-182 9 I-183 10 I-184 10 I-185 9 I-187 10 I-189 10 I-198 10 I-199 9 I-202 10 I-203 10 I-205 10 I-259 10 I-260 10 I-261 8 I-263 10 I-265 10 I-268 10 I-269 10 I-270 8 I-271 10 I-272 8 I-273 10 I-274 4 I-275 8 I-276 9 I-277 10 I-278 10 I-279 10 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-286 9 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10 I-292 10 I-293 10 I-294 9 I-297 10 I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10 I-307 8 I-328 10 I-339 10 I-462 10 I-463 10 I-464 10 I-465 10 I-466 10 I-467 10 I-468 10 I-469 10 I-470 10 I-471 10 I-472 8 I-473 8 I-474 10 I-475 10 I-476 10 I-477 10 I-478 9 I-479 10 I-480 10 II-50 7 III-50 10 III-62 10 VI-1 10 III-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 10 V-358 10 V-359 10 V-360 10 V-361 10 V-362 10 V-363 10 V-364 10 V-365 10 V-366 8 V-367 8 V-368 10 V-369 10 V-370 10 V-371 9

<Test Example 2> Test for Determining Herbicidal Activity by Field Soil Treatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of each of Echinochloa crus-galli, foxtail, Indian millet, and A. retroflexus were sowed and then covered with soil. The wettable powder produced with reference to the Formulation example 1 was diluted water, and applied on the soil surface by using a small sprayer in an amount of 1000 liters per hectare so that the effective component is 1000 g per hectare. After that, the plants were cultivated in a greenhouse, and on day 21 after the treatment, evaluation was made by the criteria described in Table 72 for determining the herbicidal effects. The results are shown in Table 77 to Table 80.

TABLE 77 Compound Echinochloacrus- No. galli I-1 8 I-2 10 I-3 10 I-4 9 I-5 10 I-9 7 I-10 10 I-11 10 I-14 10 I-16 9 I-19 8 I-27 10 I-41 9 I-43 10 I-50 10 I-51 10 I-52 10 I-53 8 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-60 10 I-61 8 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 9 I-73 9 I-74 10 I-75 9 I-76 10 I-77 9 I-78 10 I-79 9 I-80 9 I-81 9 I-82 9 I-83 9 I-84 9 I-85 9 I-86 10 I-87 9 I-88 8 I-89 9 I-90 8 I-91 9 I-92 9 I-93 7 I-98 7 I-99 8 I-105 9 I-106 10 I-107 8 I-109 9 I-110 7 I-111 9 I-115 9 I-116 10 I-117 10 I-118 10 I-119 8 I-120 8 I-125 7 I-127 10 I-128 8 I-129 9 I-131 9 I-134 10 I-135 9 I-137 10 I-138 9 I-149 8 I-167 8 I-169 10 I-179 10 I-182 7 I-184 8 I-185 9 I-187 7 I-198 7 I-199 9 I-202 10 I-203 9 I-259 10 I-260 10 I-265 10 I-269 8 I-270 8 I-271 10 I-273 9 I-274 7 I-275 8 I-276 9 I-277 8 I-278 9 I-279 7 I-280 9 I-281 9 I-282 10 I-283 9 I-284 10 I-285 10 I-286 10 I-287 10 I-288 10 I-289 9 I-292 7 I-294 9 I-297 10 I-298 7 I-299 9 I-302 7 I-303 9 I-304 10 I-307 7 I-339 8 I-471 7 I-474 7 I-475 7 I-476 7 I-477 9 I-478 9 I-479 9 I-480 8 VI-5 8 VI-7 10 V-300 7 V-365 7 V-368 7 V-369 7 V-370 7 V-371 9

TABLE 78 Compound Setaria No. viridis I-1 7 I-2 7 I-3 10 I-4 9 I-5 7 I-10 10 I-11 7 I-14 10 I-16 9 I-19 8 I-41 7 I-50 10 I-51 10 I-52 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 8 I-63 10 I-66 10 I-67 10 I-68 10 I-71 6 I-72 10 I-73 8 I-74 7 I-75 7 I-76 9 I-77 9 I-79 10 I-80 9 I-81 7 I-82 9 I-83 9 I-84 9 I-85 9 I-86 9 I-87 6 I-89 8 I-91 10 I-92 9 I-93 6 I-98 7 I-99 6 I-105 7 I-109 6 I-111 7 I-116 9 I-117 7 I-118 9 I-127 8 I-128 9 I-129 10 I-131 7 I-134 10 I-136 8 I-137 9 I-155 7 I-169 10 I-179 10 I-202 9 I-260 5 I-265 10 I-269 9 I-270 7 I-271 10 I-276 9 I-277 8 I-278 9 I-280 8 I-281 9 I-282 10 I-283 8 I-284 8 I-285 10 I-286 9 I-288 9 I-289 7 I-294 7 I-297 9 I-298 7 I-299 10 I-303 9 I-304 9 VI-7 10 VI-65 7

TABLE 79 Compound Abutilon No. theophrasti I-1 9 I-2 10 I-3 10 I-4 9 I-5 10 I-10 10 I-11 9 I-14 10 I-16 9 I-27 10 I-41 8 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 9 I-81 10 I-82 9 I-83 10 I-84 10 I-85 10 I-86 9 I-87 9 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-98 7 I-99 9 I-105 9 I-106 10 I-107 10 I-108 8 I-109 10 I-110 10 I-111 9 I-115 9 I-116 10 I-117 10 I-118 9 I-119 9 I-120 9 I-125 8 I-126 10 I-127 10 I-128 10 I-129 10 I-131 9 I-134 10 I-135 9 I-136 9 I-137 10 I-138 9 I-149 10 I-155 10 I-167 10 I-169 9 I-170 10 I-179 10 I-182 10 I-183 10 I-184 10 I-185 10 I-187 9 I-189 10 I-198 10 I-199 10 I-202 9 I-259 8 I-260 10 I-261 10 I-263 8 I-265 10 I-268 8 I-269 9 I-271 10 I-273 7 I-274 8 I-275 10 I-276 10 I-277 7 I-279 10 I-280 9 I-281 9 I-282 9 I-283 9 I-284 9 I-285 10 I-286 9 I-287 9 I-288 9 I-289 9 I-290 10 I-291 10 I-292 9 I-293 10 I-294 9 I-297 9 I-298 10 I-299 10 I-300 10 I-302 10 I-303 9 I-304 10 I-306 7 I-307 9 I-339 10 I-462 10 I-463 10 I-465 10 I-470 7 I-471 10 I-474 10 I-475 7 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 VI-1 10 VI-5 10 VI-6 9 VI-7 10 VI-65 10 V-61 8 V-300 9 V-358 10 V-361 10 V-364 7 V-365 10 V-368 10 V-369 7 V-370 10 V-371 10

TABLE 80 Compound Amaranthus No. retroflexus I-1 10 I-2 10 I-3 10 I-4 10 I-5 10 I-9 10 I-10 10 I-11 10 I-14 10 I-16 10 I-19 8 I-27 10 I-41 10 I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 9 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-87 9 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 10 I-110 10 I-111 10 I-115 9 I-116 10 I-117 10 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10 I-127 10 I-128 10 I-129 10 I-131 10 I-134 10 I-135 10 I-136 9 I-137 10 I-138 10 I-149 10 I-155 10 I-167 10 I-169 10 I-170 10 I-179 9 I-182 10 I-183 8 I-184 10 I-185 10 I-187 10 I-189 10 I-198 10 I-199 10 I-202 10 I-203 7 I-259 10 I-260 10 I-263 10 I-265 10 I-268 10 I-269 10 I-270 10 I-271 10 I-272 8 I-273 10 I-274 7 I-275 10 I-276 10 I-277 8 I-278 10 I-279 10 I-280 10 I-281 10 I-282 10 I-283 10 I-284 10 I-285 10 I-286 10 I-287 10 I-288 10 I-289 10 I-290 8 I-291 8 I-294 10 I-297 10 I-298 10 I-299 10 I-300 10 I-302 10 I-303 10 I-304 10 I-306 10 I-307 10 I-308 10 I-339 10 I-462 9 I-463 7 I-464 7 I-465 10 I-468 7 I-470 8 I-471 10 I-474 10 I-475 7 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 V-300 10 V-358 10 V-361 8 V-362 7 V-364 8 V-365 10 V-368 10 V-369 7 V-370 10 V-371 10

<Test Example 3> Test for Determining Herbicidal Activity by Field Foliage Treatment

A 80 cm² wide plastic pot was filled with a field soil and seeds of each of Indian millet and A. retroflexus were sowed and then incubated for 2 weeks in a green house. The wettable powder produced with reference to the Formulation example 1 was diluted water, and applied from the air to entire body of the plant as foliage treatment by using a small sprayer in an amount of 1000 liters per hectare so that the effective component is 1000 g per hectare. After that, the plants were cultivated in a greenhouse, and on day 14 after the treatment, evaluation was made by the criteria described in Table 72 for determining the herbicidal effects. The results are shown in Table 81 to Table 84.

TABLE 81 Compound Echinochloa No. crus-galli I-1 8 I-2 9 I-3 9 I-4 9 I-5 10 I-9 10 I-10 8 I-11 9 I-14 9 I-16 9 I-19 10 I-27 9 I-41 10 I-43 8 I-50 10 I-51 10 I-52 10 I-53 8 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 7 I-60 10 I-61 9 I-63 10 I-64 10 I-65 8 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 9 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 9 I-85 9 I-86 9 I-87 9 I-88 8 I-89 9 I-90 8 I-91 9 I-92 10 I-93 9 I-96 7 I-98 7 I-99 9 I-105 10 I-106 10 I-107 7 I-109 10 I-110 9 I-111 10 I-115 10 I-116 9 I-117 9 I-118 9 I-119 9 I-120 9 I-125 10 I-126 9 I-127 10 I-128 9 I-129 10 I-131 10 I-134 10 I-135 10 I-136 9 I-137 10 I-138 8 I-149 8 I-155 9 I-167 10 I-169 9 I-170 10 I-179 10 I-182 8 I-184 10 I-185 10 I-187 8 I-198 10 I-199 10 I-202 9 I-203 6 I-259 10 I-260 8 I-263 9 I-265 8 I-268 7 I-269 10 I-270 9 I-271 10 I-272 6 I-273 10 I-274 9 I-275 9 I-276 10 I-277 10 I-278 10 I-279 9 I-280 9 I-281 9 I-282 8 I-283 a I-284 9 I-285 9 I-286 10 I-287 8 I-288 9 I-289 9 I-292 a I-294 9 I-297 9 I-298 10 I-299 8 I-300 9 I-302 10 I-303 8 I-304 10 I-328 7 I-339 9 I-463 7 I-465 8 I-467 8 I-468 9 I-469 10 I-470 8 I-471 9 I-474 7 I-475 9 I-476 7 I-477 9 I-478 8 I-479 9 I-480 9 III-50 10 VI-1 10 VI-5 10 VI-6 8 VI-7 10 VI-65 9 VI-97 7 V-300 8 V-358 8 V-360 8 V-362 9 V-363 10 V-364 8 V-365 9 V-368 7 V-369 9 V-370 7 V-371 8

TABLE 82 Compound Setaria No. viridis I-1 8 I-2 10 I-3 9 I-4 9 I-5 10 I-10 7 I-11 9 I-14 10 I-16 9 I-19 10 I-27 6 I-41 10 I-43 8 I-50 10 I-51 10 I-52 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-60 9 I-63 10 I-66 10 I-67 10 I-68 8 I-71 9 I-72 10 I-73 10 I-74 9 I-75 10 I-76 9 I-77 10 I-78 10 I-79 10 I-80 7 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 9 I-89 10 I-90 7 I-91 10 I-92 10 I-93 9 I-105 7 I-109 7 I-116 9 I-117 9 I-118 10 I-126 7 I-127 10 I-128 10 I-129 9 I-134 10 I-136 9 I-137 10 I-138 8 I-155 7 I-167 8 I-169 9 I-179 10 I-184 8 I-185 9 I-187 8 I-199 8 I-202 9 I-261 7 I-263 9 I-265 9 I-269 8 I-271 7 I-274 8 I-275 8 I-276 10 I-277 9 I-278 10 I-281 7 I-282 7 I-284 7 I-285 9 I-286 10 I-288 10 I-289 7 I-297 9 I-298 8 I-302 10 I-303 10 I-304 10 I-328 7 I-463 7 I-464 7 I-465 10 I-468 9 I-469 10 I-470 9 I-471 10 I-475 7 I-479 7 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 7 VI-97 10 V-300 8 V-358 10 V-362 9 V-363 10 V-364 9 V-365 10 V-369 7

TABLE 83 Compound Abutilon No. theophrasti I-1 9 I-2 10 I-3 9 I-4 9 I-5 10 I-9 10 I-10 9 I-11 9 I-14 10 I-16 9 I-19 10 I-27 9 I-41 10 I-43 9 I-47 9 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-68 10 I-59 10 I-60 10 I-61 10 I-62 9 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 9 I-72 10 I-73 10 I-74 9 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 9 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-87 9 I-88 9 I-89 10 I-90 9 I-91 10 I-92 10 I-93 10 I-94 10 I-96 9 I-98 9 I-99 10 I-105 10 I-106 9 I-107 9 I-108 9 I-109 9 I-110 9 I-111 10 I-115 10 I-116 9 I-117 9 I-118 10 I-119 9 I-120 9 I-125 10 I-126 9 I-127 9 I-128 10 I-129 9 I-131 10 I-134 10 I-135 10 I-136 9 I-137 10 I-138 9 I-149 10 I-155 10 I-167 10 I-169 9 I-170 10 I-179 10 I-182 9 I-183 9 I-184 9 I-185 9 I-187 9 I-189 9 I-198 10 I-199 9 I-202 9 I-203 9 I-205 10 I-259 10 I-260 10 I-261 10 I-263 10 I-265 9 I-268 9 I-269 9 I-270 9 I-271 9 I-272 9 I-273 9 I-274 8 I-275 9 I-276 9 I-277 9 I-278 9 I-279 10 I-280 9 I-281 9 I-282 9 I-283 8 I-284 8 I-285 7 I-286 9 I-287 9 I-288 10 I-289 9 I-290 9 I-291 9 I-292 10 I-293 8 I-294 7 I-295 9 I-297 8 I-298 9 I-299 9 I-300 8 I-301 7 I-302 10 I-303 9 I-304 9 I-306 9 I-307 10 I-308 8 I-328 10 I-339 10 I-462 10 I-463 9 I-464 10 I-465 10 I-466 10 I-467 7 I-468 10 I-469 10 I-470 10 I-471 10 I-472 7 I-473 10 I-474 9 I-475 8 I-476 9 I-477 9 I-478 9 I-479 9 I-480 10 II-50 8 II-267 9 III-50 10 III-62 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 9 V-358 10 V-359 10 V-360 7 V-361 9 V-362 10 V-363 10 V-364 10 V-365 10 V-366 7 V-367 10 V-368 9 V-369 8 V-370 9 V-371 9

TABLE 84 Compound Amaranthus No. retroflexus I-1 10 I-2 10 I-3 9 I-4 9 I-5 10 I-9 10 I-10 10 I-11 10 I-14 10 I-16 10 I-19 10 I-27 9 I-41 10 I-43 10 I-47 10 I-50 10 I-51 10 I-52 10 I-53 10 I-54 10 I-55 10 I-56 10 I-57 10 I-58 10 I-59 10 I-60 10 I-61 10 I-62 10 I-63 10 I-64 10 I-65 10 I-66 10 I-67 10 I-68 10 I-71 10 I-72 10 I-73 10 I-74 10 I-75 10 I-76 10 I-77 10 I-78 10 I-79 10 I-80 10 I-81 10 I-82 10 I-83 10 I-84 10 I-85 10 I-86 10 I-87 10 I-88 10 I-89 10 I-90 10 I-91 10 I-92 10 I-93 10 I-94 10 I-96 10 I-98 8 I-99 10 I-105 10 I-106 10 I-107 10 I-108 10 I-109 9 I-110 9 I-111 10 I-315 10 I-116 8 I-117 8 I-118 10 I-119 10 I-120 10 I-125 10 I-126 10 I-127 10 I-128 10 I-129 10 I-131 10 I-134 10 I-135 10 I-136 10 I-137 10 I-138 10 I-149 10 I-155 10 I-167 10 I-169 8 I-170 19 I-179 10 I-182 9 I-183 10 I-184 10 I-185 10 I-187 10 I-189 10 I-198 10 I-199 9 I-202 9 I-203 10 I-204 7 I-205 10 I-259 10 I-260 10 I-261 10 I-263 10 I-265 10 I-268 10 I-269 10 I-270 10 I-271 10 I-272 10 I-273 10 I-274 9 I-275 9 I-276 10 I-277 10 I-278 10 I-279 10 I-280 10 I-281 9 I-282 8 I-283 8 I-284 9 I-285 8 I-286 10 I-287 10 I-288 10 I-289 10 I-290 10 I-291 10 I-292 10 I-293 10 I-294 8 I-295 8 I-297 8 I-298 10 I-299 10 I-300 10 I-301 10 I-302 10 I-303 10 I-304 10 I-306 7 I-307 9 I-328 10 I-339 10 I-462 10 I-463 10 I-464 10 I-465 10 I-466 10 I-467 10 I-468 10 I-469 10 I-470 10 I-471 10 I-472 10 I-473 3 I-474 9 I-475 9 I-476 10 I-477 10 I-478 10 I-479 10 I-480 10 II-50 10 III-50 10 III-62 10 VI-1 10 VI-5 10 VI-6 10 VI-7 10 VI-65 10 VI-97 10 V-300 10 V-358 30 V-359 10 V-360 10 V-361 10 V-362 10 V-363 10 V-364 10 V-366 10 V-366 10 V-368 9 V-369 9 V-370 10 V-371 10

As a result of the tests, it was found that the compounds of the invention have an excellent herbicidal activity. 

1-12. (canceled)
 13. A triazine derivative or a salt thereof represented by following Formula 2:

wherein B represents a hydroxyl group or a C₁-C₆ alkoxy group; R¹ represents a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; an amino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylamino C₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a hydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a phenoxyimino C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a (R³¹R³²N—C═O) C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; Y and Z represent an oxygen atom or a sulfur atom; R³¹ and R³² each independently represent a C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a benzyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl group; a C₁-C₁₀ alkylthio carbonyl group; a C₁-C₆ alkoxycarbonyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom; wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom; a hydroxyl group; a C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a C₁-C₆ haloalkylthio group; a C₁-C₆ haloalkylsulfinyl group; a C₁-C₆ haloalkylsulfonyl group; an amino group; a C₁-C₆ alkylcarbonylamino group; a mono(C₁-C₆ alkyl)amino group; a di(C₁-C₆ alkyl)amino group; a hydroxy C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy C₁-C₆ alkoxy group; a cyano C₁-C₆ alkoxy group; a C₁-C₆ acyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a carboxyl group; a C₁-C₆ alkoxycarbonyl group; a carbamoyl group; a mono(C₁-C₆ alkyl)aminocarbonyl group; a di(C₁-C₆ alkyl)aminocarbonyl group; a nitro group; a cyano group; a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; and a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and “substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₁-C₆ alkoxy group, and a C₁-C₆ haloalkoxy group.
 14. The triazine derivative or the salt thereof according to claim 13, wherein Y in Formula 2 is an oxygen atom, R¹ in Formula 2 represents a group selected from a group consisting of a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the Substituent group α; a phenyl C₁-C₆ alkyl group; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; and R² in Formula 2 represents a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α.
 15. The triazine derivative or the salt thereof according to claim 14, wherein Y in Formula 2 is an oxygen atom, R¹ in Formula 2 represents a group selected from a group consisting of a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and piperazinyl group, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; R² is a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; and a pyridyl group; and, “substituent group α” represents a group selected from a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.
 16. The triazine derivative or a salt thereof of claim 13, wherein Y and Z are each oxygen, R¹ is 4-F-Ph, R² is Me, and B is ethoxy.
 17. The triazine derivative or a salt thereof of claim 13, wherein Y and Z are each oxygen, R¹ is 4-F-Ph, R² is Me, and B is OH.
 18. A method of preparing a compound of Formula 13b, comprising treating a compound of Formula 13a with a sulfurizing agent,

wherein R¹ represents a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; an amino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylamino C₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a hydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy c₁-c₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a phenoxyimino C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a (R³¹R³²N—C═O) C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; Z represent an oxygen atom or a sulfur atom; R³¹ and R³² each independently represent a C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a benzyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl group; a C₁-C₁₀ alkylthio carbonyl group; a C₁-C₆ alkoxycarbonyl group; a C₁-C₆ haloalkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl group; a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R³¹ and R³² may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom; wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom; a hydroxyl group; a C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyloxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₁-C₆ alkylcarbonyloxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a C₁-C₆ haloalkylthio group; a C₁-C₆ haloalkylsulfinyl group; a C₁-C₆ haloalkylsulfonyl group; an amino group; a C₁-C₆ alkylcarbonylamino group; a mono(C₁-C₆ alkyl)amino group; a di(C₁-C₆ alkyl)amino group; a hydroxy C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkoxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy C₁-C₆ alkoxy group; a cyano C₁-C₆ alkoxy group; a C₁-C₆ acyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a carboxyl group; a C₁-C₆ alkoxycarbonyl group; a carbamoyl group; a mono(C₁-C₆ alkyl)aminocarbonyl group; a di(C₁-C₆ alkyl)aminocarbonyl group; a nitro group; a cyano group; a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β; and a C₃-C₆ alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group; and “substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₁-C₆ alkoxy group, and a C₁-C₆ haloalkoxy group.
 19. The method of claim 18, wherein Z is an oxygen atom, R¹ represents a group selected from a group consisting of a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group; and a heterocyclic group selected from the group consisting of pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, thiazolyl group, isoxazolyl group, pyrazolyl group, morpholinyl group, thiomorpholinyl group, and piperazinyl group, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; R² is a group selected from a group consisting of a C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; and a pyridyl group; and, “substituent group α” represents a group selected from a group consisting of a halogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₁-C₆ haloalkyl group; a C₁-C₆ alkoxy group; a C₁-C₆ haloalkoxy group; a C₁-C₆ alkylthio group; a C₁-C₆ alkylsulfinyl group; a C₁-C₆ alkylsulfonyl group; a nitro group; a cyano group; a phenyl group; and a methylenedioxy group.
 20. The method of claim 19, wherein R¹ is 4-F-Ph, and R² is Me.
 21. A method of preparing a compound of Formula 1a, comprising reacting at least one of a compound of Formula 5a and a compound of Formula 5b with a cyano compound in the presence of a base,

wherein R¹ represents a hydrogen atom; a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; an amino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylamino C₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a hydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a phenoxyimino C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C₁-C₆ alkoxy)C₁-C₆ alkyl group; a (R³¹R³²N—C═O)C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α, Y and Z represent an oxygen atom or a sulfur atom, A₁ represents a group represented by the following formula

A₂ represents a group represented by the following formula

A₃ represents a group represented by the following formula

n represents 0, 1, or 2, R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group, wherein, R⁵ and R⁸ may be joined together to form a C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain to form a ring with adjacent carbon atoms, and R⁷, R³³, and R³⁴ each independently represent a hydrogen atom, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, or a C₁-C₆ alkoxy group.
 22. The method of claim 21, wherein the cyano compound is selected from the group consisting of potassium cyanide, sodium cyanide, acetone cyanohydrin, hydrogen cyanide, and a polymer supported with hydrogen cyanide.
 23. The method of claim 21, wherein the reaction proceeds in the presence of a phase transfer catalyst.
 24. The method of claim 21, wherein Y and Z are each an oxygen atom.
 25. The method of claim 21, wherein R¹ is 4-F-Ph, and R² is Me.
 26. A method of preparing a compound of Formula 1a, comprising reacting a compound of Formula 3 with a compound of Formula 4c,

wherein R¹ represents a hydrogen atom; a C₁-C₁₂ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₃-C₆ cycloalkenyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₃-C₆ halocycloalkyl group; a C₃-C₆ halocycloalkyl C₁-C₆ alkyl group; an amino C₁-C₆ alkyl group; a nitro C₁-C₆ alkyl group; a C₁-C₆ alkylamino C₁-C₆ alkyl group; a di(C₁-C₆ alkyl)amino C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylthio C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfinyl C₁-C₆ alkyl group; a C₁-C₆ haloalkylsulfonyl C₁-C₆ alkyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a hydroxy C₁-C₆ alkyl group; a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy C₁-C₆ alkyl group; a phenyloxy C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylthio C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfinyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenylsulfonyl C₁-C₆ alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ haloalkoxy C₁-C₆ alkyl group; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α; a C₁-C₆ alkoxyimino C₁-C₆ alkyl group; a phenoxyimino C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a di(C₁-C₆ alkoxy)C₁-C₆ alkyl group; a (R³¹R³²N—C═O)C₁-C₆ alkyl group; a C₁-C₆ alkoxycarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group; a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group; a C₁-C₆ alkylidene aminooxy C₁-C₆ alkyl group; a formyl C₁-C₆ alkyl group; a C₁-C₆ alkylthio C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfinyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₁-C₆ alkylsulfonyl C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkoxy C₁-C₆ alkyl group; a cyano C₁-C₆ alkyl group; a C₂-C₆ alkylidene amino group; a di(C₁-C₁₀ alkyl)amino C₁-C₆ alkylidene amino group; a NR³¹R³² group; a C₁-C₆ alkoxy group; a C₂-C₆ alkenyloxy group; a C₂-C₆ alkynyloxy group; a C₃-C₆ cycloalkyloxy group; a C₃-C₆ cycloalkyl C₁-C₆ alkyloxy group; a C₁-C₆ haloalkoxy group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone; a C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; or a C₁-C₆ alkoxy C₁-C₆ alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; R² represents a hydrogen atom; a C₁-C₆ alkyl group; a C₂-C₆ alkenyl group; a C₂-C₆ alkynyl group; a C₃-C₆ cycloalkyl group; a C₁-C₆ haloalkyl group; a C₂-C₆ haloalkenyl group; a C₂-C₆ haloalkynyl group; a C₁-C₆ alkoxy C₁-C₆ alkyl group; a C₃-C₆ cycloalkyloxy C₁-C₆ alkyl group; a di(C₁-C₆ alkoxy) C₁-C₆ alkyl group; a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α; a phenyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₁-C₆ alkyl group which may be substituted with one or more substituents selected from the substituent group α; a phenyl C₂-C₆ alkenyl group which may be substituted with one or more substituents selected from the substituent group α; or a phenyl C₂-C₆ alkynyl group which may be substituted with one or more substituents selected from the substituent group α, Y and Z represent an oxygen atom or a sulfur atom, A₁ represents a group represented by the following formula

A₂ represents a group represented by the following formula

A₃ represents a group represented by the following formula

n represents 0, 1, or 2, R⁵, R⁶, R⁸, R⁹, R³⁵ and R³⁶ each independently represent a hydrogen atom or a C₁-C₆ alkyl group, wherein, R⁵ and R⁸ may be joined together to form a C₂-C₅ alkylene chain or a C₂-C₅ alkenylene chain, and may form a ring together with adjacent carbon atoms, and R⁵ and R³⁵ may be joined together to form a C₁-C₅ alkylene chain to form a ring with adjacent carbon atoms, and R⁷, R³³, and R³⁴ each independently represent a hydrogen atom, a C₁-C₆ alkyl group, a C₁-C₆ haloalkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, or a C₁-C₆ alkoxy group.
 27. The method of claim 26, wherein Y and Z are each an oxygen atom.
 28. The method of claim 26, wherein the reaction proceeds in the presence of a Lewis acid.
 29. The method of claim 26, wherein the reaction proceeds in the presence of a base.
 30. The method of claim 26, wherein R¹ is 4-F-Ph, and R² is Me. 